The Anion-Binding Approach to Catalytic Enantioselective Acyl Transfer

Abstract

This account details the development of a dual-catalysis approach and its application to the kinetic resolution of amines and other enantioselective acyl-transfer reactions. Anion recognition is an essential design element of these processes, which are enabled by the combined action of an achiral 4-(N,N-dimethylamino)pyridine (DMAP) derivative and a chiral anion receptor catalyst.

1 Introduction

2 Kinetic Resolution of Amines

2.1 Benzylic Amines

2.2 Propargylic Amines

2.3 Allylic Amines

2.4 Benzylic Amines Revisited

2.5 Racemic Diamines

3 Desymmetrization of meso-Diamines

4 Miscellaneous Acyl Transfer Reactions

4.1 Steglich Reaction

4.2 Reactions of Isoquinolines with Azlactones

4.3 Acylation of Silyl Ketene Acetals

5 Conclusions

Key words

asymmetric catalysis - amines - acylation - kinetic resolution - desymmetrization

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