Synlett 2013; 24(4): 529-530
DOI: 10.1055/s-0032-1318133
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© Georg Thieme Verlag Stuttgart · New York

α-Amido Sulfones as Imine Precursors in Enantioselective Nucleophilic Additions

Alicia Monleón
Departament de Química Orgànica, Facultat de Química, Universitat de València, C/ Dr. Moliner 50, 46100 Burjassot, Spain   Email: alicia.monleon@uv.es
› Author Affiliations
Further Information

Publication History

Publication Date:
30 January 2013 (online)

Introduction

α-Amido sulfones have emerged as valuable precursors of imines in enantioselective nucleophilic addition reactions because their use offers several advantages.[ 1 ] Imines are generated in situ from α-amido sulfones by the elimination of the sulfone group under basic or acid conditions. The in situ formation avoids the competitive enolization process that often occurs when using imines and which hinders an effective nucleophilic addition. Moreover, unlike imines, α-amido sulfones are stable solids which can be easily synthesized and stored for a long period of time.

 
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