European Journal of Organic Chemistry

Highly Diastereo??and Enantioselective Aldol Reactions in Common Organic Solvents Using N??Arylprolinamides as Organocatalysts with Enhanced Acidity

JN Moorthy, S Saha

Index: Moorthy, Jarugu Narasimha; Saha, Satajit European Journal of Organic Chemistry, 2009 , # 5 p. 739 - 748

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Citation Number: 24

Abstract

Abstract A broad set of N-arylprolinamides 1–8 with increasing NH acidity and steric crowding has been synthesized and its catalytic activity explored for enantioselective aldol reactions. In DMF containing 10 mol-% of TFA, all arylamides are found to catalyze the reaction between cyclohexanone and a variety of electrophilic aldehydes leading to aldols in excess of 90% yield and> 95% enantioselectivity. The perfluorophenyl catalyst 8 is ...