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Asymmetric Michael and Aldol additions using bifunctional cinchona-alkaloid-based catalysts
   
Document Number
US Patent 7312335
Issued Date
December 25, 2007
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Inventors
Deng; Li (Newton, MA)
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Abstract
One aspect of the present invention relates to quinine-based and quinidine-based catalysts. Another aspect of the invention relates to a method of preparing a derivatized quinine-based or quinidine-based catalyst comprising 1) reacting quinine or quinidine with base and a compound that has a suitable leaving group, and 2) converting the ring methoxy group to a hydroxy group. Another aspect of the present invention relates to a method of preparing a chiral, non-racemic compound from a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone, comprising the step of: reacting a prochiral electron-deficient alkene or azo compound or prochiral aldehyde or prochiral ketone with a nucleophile in the presence of a catalyst; thereby producing a chiral, non-racemic compound; wherein said catalyst is a derivatized quinine or quinidine. Another aspect of the present invention relates to a method of kinetic resolution, comprising the step of: reacting racemic chiral alkene with a nucleophile in the presence of a derivatized quinine or quinidine.
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Number of Claims:
74
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Owner
Brandeis University (Waltham, MA)
Published
December 25, 2007
Application Number
11/140,574
Filed
May 27, 2005
US Classification
546/135   546/134 546/136
Int'l Classification
C07D   453/02   (20060101)   C07D   453/04   (20060101)  
Assistant Examiner
Parent Case
RELATED APPLICATIONS This application claims the benefit of priority to U.S. Provisional Patent Application Ser. No. 60/576,754, filed Jun. 3, 2004; and U.S. Provisional Patent Application Ser. No. 60/592,500, filed Jul. 30, 2004.
USPTO Field of Search
546/134   546/135   546/136  
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