The Journal of Organic Chemistry

Complete control of the rearrangement modes of enolates of. alpha.-allyloxy ketones: reversal from the [3, 3]-Claisen to the [2, 3]-Wittig pathway by the use of the …

JI Luengo, M Koreeda

Index: Luengo, Juan I.; Koreeda, Masato Journal of Organic Chemistry, 1989 , vol. 54, # 23 p. 5415 - 5417

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Citation Number: 7

Abstract

Summary: It has been shown that the predilection for the [3, 3]-Claisen rearrangement pathway of enolates of a-allyloxy ketones is cleanly overridden by the [2, 3]-Wittig rearrangement route with the use of carbanions of their corresponding N, N- dimethylhydrazones. Since the formation of these hydrazones as well as hydrolysis of the rearranged a-hydroxyhydrazones can be readily achieved, this approach allows a [2, 3]- ...