Tetrahedron

Application of enantiopure templated azomethine ylids to β-hydroxy-α-amino acid synthesis

…, G Hamblett, LM Harwood, SM Robertson, DJ Watkin…

Index: Alker, David; Hamblett, Giles; Harwood, Laurence M.; Robertson, Sarah M.; Watkin, David J.; Williams, C. Eleri Tetrahedron, 1998 , vol. 54, # 22 p. 6089 - 6098

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Citation Number: 61

Abstract

Chiral stabilised azomethine ylids derived from the reaction of (5S)-5-phenylmorpholin-2- one (1) with aldehydes undergo efficient and highly diastereocontrolled cycloaddition with a second molecule of aldehyde to furnish products (2) which may be converted into enantiomerically pure threo (2S, 3R) β-hydroxy-α-amino acids (3) in excellent yield.