Tetrahedron letters

Preparation of optically active α-hydroxy oxime ether by diastereoselective imino 1, 2-Wittig rearrangement of hydroximates and its application to synthesis of (+)- …

O Miyata, J Hashimoto, R Iba, T Naito

Index: Miyata, Okiko; Hashimoto, Jun; Iba, Ryuuichi; Naito, Takeaki Tetrahedron Letters, 2005 , vol. 46, # 23 p. 4015 - 4018

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Citation Number: 19

Abstract

The diastereoselective imino 1, 2-Wittig rearrangement of hydroximates provides a novel method for the construction of optically active α-hydroxy oxime ethers. Upon treatment with LDA, allyl p-methoxyphenylhydroximate carrying a chiral auxiliary smoothly underwent diastereoselective rearrangement to give the (R)-α-hydroxy oxime ether which was effectively converted into (+)-cytoxazone.