Synlett 2014; 25(6): 783-794
DOI: 10.1055/s-0033-1340618
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© Georg Thieme Verlag Stuttgart · New York

The Anion-Binding Approach to Catalytic Enantioselective Acyl Transfer

Daniel Seidel*
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, Piscataway, NJ 08854, USA   Email: seidel@rutchem.rutgers.edu
› Author Affiliations
Further Information

Publication History

Received: 14 November 2013

Accepted: 03 December 2013

Publication Date:
27 January 2014 (online)


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