Compounds and methods for preparation of diarylpropanes

Abstract

Compounds of structure (I): including stereoisomers, tautomers and salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , X, Y and Z are as defined herein. Such compounds are useful for the preparation of diarylpropane compounds. Methods for the preparation of compounds of structure (I) are also disclosed, as are methods employing compounds of structure (I) for the preparation of diarylpropanes.

1 . A compound having the following structure (I): 
       
         
           
           
               
               
           
         
       
       or a stereoisomer, tautomer or salt thereof, wherein:
 R 1 , R 2 , R 3  and R 4  are each independently hydrogen, alkyl, aryl or aralkyl; 
 one of R 5  or R 6  is oxo, and the other of R 5  or R 6  is hydrogen; and 
 X, Y and Z are each independently absent or hydrogen, or X and Y or Z and Y may join to form a bond, wherein X, Y and Z are each chosen such that all valences are satisfied. 
 
     
     
         2 . The compound of  claim 1 , wherein R 5  is oxo, R 6  is hydrogen and the compound has one of the following structures (IA) or (IB): 
       
         
           
           
               
               
           
         
       
     
     
         3 . The compound of  claim 2 , wherein each of R 1  and R 2  are alkyl. 
     
     
         4 . The compound of  claim 3 , wherein each of R 1  and R 2  are methyl and the compound has one of the following structures (IA-1) or (IB-1): 
       
         
           
           
               
               
           
         
       
     
     
         5 . The compound of  claim 2 , wherein each of R 3  and R 4  are aralkyl. 
     
     
         6 . The compound of  claim 5 , wherein each of R 3  and R 4  are benzyl and the compound has one of the following structures (IA-2) or (IB-2): 
       
         
           
           
               
               
           
         
       
     
     
         7 . The compound of  claim 2 , wherein each of R 3  and R 4  are alkyl. 
     
     
         8 . The compound of  claim 7 , wherein each of R 3  and R 4  are isopropyl and the compound has one of the following structures (IA-3) or (IB-3): 
       
         
           
           
               
               
           
         
       
     
     
         9 . The compound of  claim 2 , wherein each of R 3  and R 4  are hydrogen and the compound has one of the following structures (IA-4) or (IB-4): 
       
         
           
           
               
               
           
         
       
     
     
         10 . The compound of  claim 1 , wherein R 6  is oxo, R 5  is hydrogen and the compound has one of the following structures (IC) or (ID): 
       
         
           
           
               
               
           
         
       
     
     
         11 . The compound of  claim 10 , wherein each of R 1  and R 2  are alkyl. 
     
     
         12 . The compound of  claim 11 , wherein each of R 1  and R 2  are methyl and the compound has one of the following structures (IC-1) or (ID-1): 
       
         
           
           
               
               
           
         
       
     
     
         13 . The compound of  claim 10 , wherein each of R 3  and R 4  are aralkyl. 
     
     
         14 . The compound of  claim 13 , wherein each of R 3  and R 4  are benzyl and the compound has one of the following structures (IC-2) or (ID-2): 
       
         
           
           
               
               
           
         
       
     
     
         15 . The compound of  claim 10 , wherein each of R 3  and R 4  are alkyl. 
     
     
         16 . The compound of  claim 15 , wherein each of R 3  and R 4  are isopropyl and the compound has one of the following structures (IC-3) or (ID-3): 
       
         
           
           
               
               
           
         
       
     
     
         17 . The compound of  claim 10 , wherein each of R 3  and R 4  are hydrogen and the compound has one of the following structures (IC-4) or (ID-4): 
       
         
           
           
               
               
           
         
       
     
     
         18 . The compound of  claim 1 , wherein at least one of R 3  or R 4  is allyl. 
     
     
         19 . The compound of  claim 18 , wherein each of R 3  and R 4  are allyl. 
     
     
         20 - 27 . (canceled) 
     
     
         28 . A method for preparing a compound of structure (II): 
       
         
           
           
               
               
           
         
       
       or a stereoisomer, tautomer or salt thereof, wherein:
 R 7 , R 8 , R 9  and R 10  are each independently hydrogen, alkyl, aryl or aralkyl, the method comprising reducing a compound of structure (I): 
 
       
         
           
           
               
               
           
         
       
       or a stereoisomer, tautomer or salt thereof, wherein:
 R 1 , R 2 , R 3  and R 4  are each independently hydrogen, alkyl, aryl or aralkyl; 
 one of R 5  or R 6  is oxo, and the other of R 5  or R 6  is hydrogen; and 
 X, Y and Z are each independently absent or hydrogen, or X and Y or Z and Y may join to form a bond, wherein X, Y and Z are each chosen such that all valences are satisfied. 
 
     
     
         29 - 59 . (canceled)