[1,2]-Wittig Rearrangement: Stereochemical Features and Synthetic Utilities

Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journalArticle

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Abstract

The stereochemical features and synthetic potentials are described of the classic [1,2]-Wittig rearrangement which is now recognized to proceed via the radical cleavage-recombination mechanism. First, the [1,2]-Wittig rearrangement of enantio-defined α-benzyloxypropyllithium and its (R)-α-methylbenzyloxy analogs is shown to proceed predominantly with inversion of configuration at the Li-bearing terminus and retention of configuration at the migrating carbon. Second, the [1,2]-Wittig rearrangement of O-glycosides of both acetal and ketal types, including those derived from D-ribose and D-glucose, is demonstrated to proceed with complete retention of either the α- or β-anomeric configuration, along with efficient stereocontrol over the newly created chiral center on the side chain to afford the novel classes of stereo-defined C-glycosides in good yields.

Original languageEnglish
Pages (from-to)126-134
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume54
Issue number11
Publication statusPublished - Dec 1 1996

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Bearings (structural)
Acetals
Ribose
Glycosides
Carbon
Glucose
C-glycoside

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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[1,2]-Wittig Rearrangement : Stereochemical Features and Synthetic Utilities. / Tomooka, Katsuhiko; Nakai, Takeshi.

In: Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, Vol. 54, No. 11, 01.12.1996, p. 126-134.

Research output: Contribution to journalArticle

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