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 journalArticlepeer-review

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

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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