US2011117649A1PendingUtilityA1

Catalytic enantioselective synthesis of flavanones and chromanones

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Assignee: SCHEIDT KARLPriority: Feb 29, 2008Filed: Dec 13, 2010Published: May 19, 2011
Est. expiryFeb 29, 2028(~1.6 yrs left)· nominal 20-yr term from priority
C07D 311/22C07D 311/32C07D 311/92
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Claims

Abstract

Various chromanone, flavanone and abyssinone compounds as can be prepared enantioselectively using a chiral thiourea catalyst.

Claims

exact text as granted — not AI-modified
1 - 7 . (canceled) 
     
     
         8 . A composition comprising compounds of a formula 
       
         
           
           
               
               
           
         
       
       wherein R 1  is selected from substituted or unsubstituted alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkylalkenyl, aryl, and aralkyl moieties; R 3 , R 4 , R 5 , and R 6  are independently selected from H, OR 7 , substituted a unsubstituted alkyl and cycloalkyl moieties, and moieties where one of R 6  and R 5  together, R 5  and R 4  together, or R 4  and R 3  together form a substituted or unsubstituted C 3  to about C 5  alkylene or alkenylene moieties; and R 7  is selected from H and substituted or unsubstituted alkyl moieties, said composition comprising at least about an 80% enantiomeric excess of one of the (R)- and (S)-enantiomers of a said compound. 
     
     
         9 . The composition of  claim 8  wherein R 1  is selected from phenyl and substituted phenyl moieties. 
     
     
         10 . The composition of  claim 9  wherein said substituents are selected from hydroxy, alkyl, alkoxy, alkylene and halide moieties and combinations of said moieties. 
     
     
         11 . The composition of  claim 10  wherein R 1  is selected from 
       
         
           
           
               
               
           
         
       
       moieties. 
     
     
         12 . The composition of  claim 8  wherein the (R)-enantiomer is of a formula 
       
         
           
           
               
               
           
         
       
     
     
         13 . The composition of  claim 12  wherein R 1  is selected from phenyl and substituted phenyl moieties. 
     
     
         14 . The composition of  claim 13  wherein R 1  is selected from 
       
         
           
           
               
               
           
         
       
       moieties. 
     
     
         15 . The composition of  claim 8  incorporated into a medium comprising pancreatic tumor cells. 
     
     
         16 . A compound of a formula 
       
         
           
           
               
               
           
         
       
       wherein R 1  is selected from substituted or unsubstituted alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkylalkenyl, aryl, and aralkyl moieties; R 3 , R 4 , R 5 , and R 6  are independently selected from H, OR 7 , substituted a unsubstituted alkyl and cycloalkyl moieties, and moieties where one of R 6  and R 5  together, R 5  and R 4  together, or R 4  and R 3  together form a substituted or unsubstituted C 3  to about C 5  alkylene or alkenylene moieties; and R 7  is selected from H and substituted or unsubstituted alkyl moieties. 
     
     
         17 . The compound of  claim 16  wherein R 1  is selected from phenyl and substituted phenyl moieties. 
     
     
         18 . The compound of  claim 17  wherein said substituents are selected from hydroxy, alkyl, alkoxy, alkylene and halide moieties and combinations of said moieties. 
     
     
         19 . The compound of  claim 18  wherein R 1  is selected from 
       
         
           
           
               
               
           
         
       
       moieties. 
     
     
         20 . A compound of a formula 
       
         
           
           
               
               
           
         
       
       wherein R 1  is selected from substituted or unsubstituted alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, cycloalkylalkenyl, and aralkyl moieties; R 3 , R 4 , R 5 , and R 6  are independently selected from H, OR 7 , substituted a unsubstituted alkyl and cycloalkyl moieties, and moieties where one of R 6  and R 5  together, R 5  and R 4  together, or R 4  and R 3  together form a substituted or unsubstituted C 3  to about C 5  alkylene or alkenylene moieties; and R 7  is selected from H and substituted or unsubstituted alkyl moieties. 
     
     
         21 . A compound of a formula 
       
         
           
           
               
               
           
         
         wherein R 1  is selected from 
       
       
         
           
           
               
               
           
         
       
       moieties. 
     
     
         22 . The compound of  claim 21  incorporated into a medium comprising pancreatic tumor cells.

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