Tetrahedron letters

Asymmetric halogenation of chiral imide enolates. A general approach to the synthesis of enantiomerically pure α-amino acids.

DA Evans, JA Ellman, RL Dorow

Index: Evans, David A.; Ellman, Jon A.; Dorow, Roberta L. Tetrahedron Letters, 1987 ,  vol. 28,  # 11  p. 1123 - 1126

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Citation Number: 138

Abstract

Abstract The chiral N-acyl oxazolidones 2, as the derived dibutyl boron enolates, have been demonstrated to undergo diastereoselective bromination and subsequent azide displacement to give the α-azido carboximides 4a (5 cases). These adducts may be hydrolyzed under mild conditions to the enantiomerically pure α-azido carboxylic acids 5a.