Tetrahedron

[2, 3]-Wittig sigmatropic rearrangement of crotyl propargyl ether system. An emerging tool for control of acyclic stereochemistry

K Mikami, KI Azuma, T Nakai

Index: Mikami, Koichi; Azuma, Ken-Ichi; Nakai, Takeshi Tetrahedron, 1984 , vol. 40, # 12 p. 2303 - 2308

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Citation Number: 51

Abstract

The [2, 3]-Wittig rearrangement of properly designated (E)-and (Z)-crotyl propargyl ether system has been shown to exhibit a remarkably high degree of threo-and erythro-selection, respectively, and the stereochemical outcomes are discussed on mechanistic grounds. Some useful transformations of the rearrangement product are also described within the context of the formal total synthesis of (±)-oudemansin. Further, the high level of ...