Organic letters

Asymmetric Lewis acid mediated [1, 2]-rearrangement of proline-derived ammonium ylides

P Tuzina, P Somfai

Index: Tuzina, Pavel; Somfai, Peter Organic Letters, 2009 , vol. 11, # 4 p. 919 - 921

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Citation Number: 14

Abstract

The first example of asymmetric Lewis acid mediated [1, 2]-rearrangement of N-benzylic proline amides to form quaternary proline derivatives is reported. The presented reaction is shown to proceed with remarkable high C→ N→ C chirality transfer. Various quaternary proline derivatives have been prepared in good to excellent yields and high enantiomeric purity.

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