US2021053043A1PendingUtilityA1

Olefin metathesis catalysts

63
Assignee: UMICORE AG & CO KGPriority: Dec 10, 2015Filed: Nov 10, 2020Published: Feb 25, 2021
Est. expiryDec 10, 2035(~9.4 yrs left)· nominal 20-yr term from priority
Inventors:Adam M. JohnsT. Patrick MontgomeryTonia S. AhmedRobert H. GrubbsRichard L. Pederson
B01J 2231/54C07C 6/02B01J 2531/821C07C 2531/22B01J 31/2278B01J 31/2295C07C 6/06C07C 6/04B01J 31/2273B01J 31/22B01J 31/226B01J 2231/543
63
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Claims

Abstract

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

Claims

exact text as granted — not AI-modified
1 .- 8 . (canceled) 
     
     
         9 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         wherein: 
         X is O or S; 
         Y is O or S; 
         Z is N or CR 32 ; 
         W is O, NR 33  or S; 
         R 1  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 2  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl, optionally substituted C 3-8  cycloalkenyl or together with R 3  may form a polycyclic ring; 
         R 3  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl or together with R 2  may form a polycyclic ring; 
         R 4  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 5  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 6  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 7  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 8  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 9  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 10  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 11  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 12  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 13  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 14  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 16  may form an optionally substituted polycyclic ring; 
         R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
         R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 18  may form an optionally substituted polycyclic ring; 
         R 18  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 17  may form an optionally substituted polycyclic ring; 
         R 19  is hydrogen, optionally substituted C 1-24  alkyl, —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 20  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 21  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 22  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 23  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 24  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 25  is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, 
         R 26  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 27  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 28  is H, optionally substituted C 1-8  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 29  is hydrogen, optionally substituted C 1-24  alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 30  is optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 31  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 32  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
         R 33  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; and 
         m is 1 or 2. 
       
     
     
         10 . The compound of  claim 9  wherein
 X is O or S; 
 Y is O or S; 
 Z is N or CR 32 ; 
 W is O, NR 33  or S; 
 R 1  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 2  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl, optionally substituted C 3-8  cycloalkenyl or together with R 3  may form a polycyclic ring; 
 R 3  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl or together with R 2  may form a polycyclic ring; 
 R 4  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 5  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 6  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 7  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 8  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 9  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 10  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 11  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 12  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 13  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 14  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 18  may form a polycyclic ring; 
 R 18  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 17  may form a polycyclic ring; 
 R 19  is hydrogen, optionally substituted C 1-24  alkyl, —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 20  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 21  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 22  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 23  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 24  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 25  is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, 
 R 26  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 27  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 28  is H, optionally substituted C 1-8  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 29  is hydrogen, optionally substituted C 1-24  alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 30  is optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 31  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 32  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 33  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; and m is 1 or 2. 
 
     
     
         11 . The compound of  claim 9  wherein
 X is S; 
 Y is S; 
 Z is N or CR 32 ; 
 W is O; 
 R 1  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 2  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl, optionally substituted C 3-8  cycloalkenyl or together with R 3  may form a polycyclic ring; 
 R 3  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl or together with R 2  may form a polycyclic ring; 
 R 4  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 5  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 6  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 7  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 8  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 9  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 10  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 11  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 12  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 13  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 14  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 16  may form an optionally substituted polycyclic ring; 
 R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
 R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 18  may form an optionally substituted polycyclic ring; 
 R 18  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 17  may form an optionally substituted polycyclic ring; 
 R 19  is hydrogen, optionally substituted C 1-24  alkyl, —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 20  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 21  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 22  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 23  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 24  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 25  is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, 
 R 26  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 27  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 28  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 29  is hydrogen, optionally substituted C 1-24  alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 30  is optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 31  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 32  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; and m is 1 or 2. 
 
     
     
         12 . The compound of  claim 9  wherein
 X is S; 
 Y is S; 
 Z is N; 
 W is O; 
 R 1  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 2  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl, optionally substituted C 3-8  cycloalkenyl or together with R 3  may form a polycyclic ring; 
 R 3  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl or together with R 2  may form a polycyclic ring; 
 R 4  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 5  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 6  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 7  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 8  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 9  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 10  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 11  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 12  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 13  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 14  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 16  may form an optionally substituted polycyclic ring; 
 R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
 R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 18  may form an optionally substituted polycyclic ring; 
 R 18  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 17  may form an optionally substituted polycyclic ring; 
 R 19  is hydrogen, optionally substituted C 1-24  alkyl, —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 20  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 21  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 22  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 23  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 24  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 25  is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, 
 R 26  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 27  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 28  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 29  is hydrogen, optionally substituted C 1-24  alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 30  is optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 31  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 32  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; and m is 1 or 2. 
 
     
     
         13 . The compound of  claim 9  wherein
 X is S; 
 Y is S; 
 Z is CR 32 ; 
 W is O; 
 R 1  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 2  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl, optionally substituted C 3-8  cycloalkenyl or together with R 3  may form a polycyclic ring; 
 R 3  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl or together with R 2  may form a polycyclic ring; 
 R 4  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 5  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 6  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 7  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 8  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 9  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 10  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 11  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 12  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 13  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 14  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 16  may form an optionally substituted polycyclic ring; 
 R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
 R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
 R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 17  may form an optionally substituted polycyclic ring; 
 R 19  is hydrogen, optionally substituted C 1-24  alkyl, —C(O)R 25 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 20  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 21  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 22  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 23  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 24  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 25  is OH, OR 30 , NR 27 R 28 , optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, 
 R 26  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 27  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 28  is H, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 29  is hydrogen, optionally substituted C 1-24  alkyl, OR 26 , —NR 27 R 28 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 30  is optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 31  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; 
 R 32  is hydrogen, optionally substituted C 1-24  alkyl, optionally substituted C 3-8  cycloalkyl, optionally substituted heterocycle, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl; and m is 1 or 2. 
 
     
     
         14 . The compound of  claim 9  wherein
 X is S; 
 Y is S; 
 
       
         
           
           
               
               
           
         
       
       of Formula (I) is 
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
       
       of Formula (I) is 
       
         
           
           
               
               
           
         
         R 20  is H; and 
         R 15  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 16  may form an optionally substituted polycyclic ring; 
         R 16  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 15  may form an optionally substituted polycyclic ring; 
         R 17  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, optionally substituted C 3-8  cycloalkyl, optionally substituted C 5-24  aryl or optionally substituted C 3-8  cycloalkenyl, or together with R 18  may form an optionally substituted polycyclic ring; 
         R 18  is hydrogen, optionally substituted C 1-24  alkyl, halogen, —C(O)R 25 , —OR 26 , CN, —NR 27 R 28 , NO 2 , —CF 3 , —S(O) m R 29 , —P(O)(OH) 2 , —OP(O)(OH) 2 , —SR 31 , optionally substituted heterocycle, 
       
     
     
         15 . The compound of  claim 9 , wherein 
       
         
           
           
               
               
           
         
       
       of Formula (I) is 
       
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
       
       of Formula (I) 
       
         
           
           
               
               
           
         
         R 20  is H; and 
       
       
         
           
           
               
               
           
         
       
       of Formula (I) is 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         16 . The compound of  claim 15 , wherein 
       
         
           
           
               
               
           
         
       
       of Formula (I) is 
       
         
           
           
               
               
           
         
       
     
     
         17 . A method for performing a cross metathesis reaction, comprising: contacting a first olefin reactant with a second olefin reactant in the presence of a compound according to  claim 9 , under conditions effective to promote the formation of at least one cross metathesis product. 
     
     
         18 . The method according to  claim 17 , wherein the first olefin reactant and the second olefin reactant are the same. 
     
     
         19 . The method according to  claim 17 , wherein the first olefin reactant and the second olefin reactant are different. 
     
     
         20 . The method according to  claim 17 , wherein the first olefin reactant and the second olefin reactant are each in a Z-configuration. 
     
     
         21 . The method according to  claim 20 , wherein the at least one cross metathesis product is greater than about 80% Z. 
     
     
         22 . The method according to  claim 17 , wherein the first olefin reactant and the second olefin reactant are each in an E-configuration. 
     
     
         23 . The method according to  claim 22 , wherein the at least one cross metathesis product is greater than about 80% E.

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