Wittig Rearrangement of α-(Propargyloxy)alkyllithiums

Periselectivity and Steric Course at the Lithium-Bearing Terminus

Katsuhiko Tomooka, Nobuyuki Komine, Takeshi Nakai

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.

Original languageEnglish
Pages (from-to)1045-1046
Number of pages2
JournalSynlett
Volume1997
Issue number9
DOIs
Publication statusPublished - Jan 1 1997
Externally publishedYes

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Bearings (structural)
Lithium
butyllithium
stannane

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Wittig Rearrangement of α-(Propargyloxy)alkyllithiums : Periselectivity and Steric Course at the Lithium-Bearing Terminus. / Tomooka, Katsuhiko; Komine, Nobuyuki; Nakai, Takeshi.

In: Synlett, Vol. 1997, No. 9, 01.01.1997, p. 1045-1046.

Research output: Contribution to journalArticle

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