[1,2]-Wittig rearrangement

Stereochemical features and synthetic utilities

Katsuhiko Tomooka, Takeshi Nakai

Research output: Contribution to journalArticle

21 Citations (Scopus)

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)1000-1008
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume54
Issue number11
DOIs
Publication statusPublished - Jan 1 1996
Externally publishedYes

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

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

[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, 01.01.1996, p. 1000-1008.

Research output: Contribution to journalArticle

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