The Journal of Organic Chemistry

Asymmetric induction in nitrone cycloadditions: a total synthesis of acivicin by double asymmetric induction

S Mzengeza, RA Whitney

Index: Mzengeza, Shadreck; Whitney, Ralph Allen Journal of Organic Chemistry, 1988 ,  vol. 53,  # 17  p. 4074 - 4081

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Citation Number: 72

Abstract

A total synthesis of acivicin,(aS, 5S)-a-amino-3-chloro-4, 5-dihydroisoxazole-5-acetic acid, has been achieved in 39% overall yield from a derivative of (2s)-vinylglycine. The required diastereomer was obtained in an extremely efficient manner (I 19: l) through double asymmetric induction in the reaction of a (2s)-vinylglycine derivative with a chiral, nonracemic N-glycosylnitrone derived from D-ribose. The origin of the asymmetric ...