Tetrahedron

Preparation of non-racemic single-stereocentre α-aminonitriles and a study of their fate in Bruylants reactions

V Beaufort-Droal, E Pereira, V Théry, DJ Aitken

Index: Beaufort-Droal, Virginie; Pereira, Elisabeth; Thery, Vincent; Aitken, David J. Tetrahedron, 2006 , vol. 62, # 51 p. 11948 - 11954

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Citation Number: 13

Abstract

A number of chiral carboxamide dehydration methods were investigated for the preparation of four representative enantiomerically enriched α-aminonitriles possessing only one stereogenic centre; best results were observed using Burgess' salt (yield up to 87%, er up to 92/8) or the trifluoroacetic anhydride–triethylamine combination (yield up to 98%, er up to 86/14). Two of the aminonitriles thus obtained were subjected to Bruylants reactions with a ...