The Journal of Organic Chemistry

Chiral base-induced [2, 3] Wittig rearrangement of acyclic. alpha.-(propargyloxy) acetic acids and amides

JA Marshall, XJ Wang

Index: Marshall, James A.; Wang, Xiao-jun Journal of Organic Chemistry, 1992 , vol. 57, # 9 p. 2747 - 2750

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Citation Number: 22

Abstract

Base-initiated [2, 3] sigmatropic rearrangements have only recently been employed to effect stereoselective transformations in acyclic systems.'Rearrangements of allylic ethers ([2, 3] Wittig)* and sulfonium salts are especially important as they effect carbon chain homologation, often with high diastereoselectivity. Nonracemic allylic ethers and sulfonium salts rearrange with eseentially complete l, &stereocenter transfer." In some cases chiral ...