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Synthesis 1991; 1991(8): 594-604
DOI: 10.1055/s-1991-26523
review
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Acyclic Stereocontrol via [2,3]-Wittig Sigmatropic Rearrangement

Koichi Mikami* , Takeshi Nakai
  • *Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo 152, Japan
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Publication Date:
29 April 2002 (online)

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[2,3]-Sigmatropic rearrangement, which involves an oxycarbanion as the migrating terminus, which is now known as the [2,3]-Wittig rearrangement, is reviewed, highlighting acyclic stereocontrol and natural product synthesis. 1. Introduction 2. Scope and Limitations 2.1. Substrate Variations 2.2. Regioselection in Carbanion Generation 3. Acyclic Stereocontrol 3.1. Basic Transition State Conformation 3.2. Diastereoselection 3.3. Olefinic Stereoselection 3.4. Asymmetric Synthesis 3.4.1. Chirality Transfer 3.4.2. Asymmetric Induction 3.4.3. Chiral Base 4. Sigmatropic Sequences 4.1. Remote Stereocontrol