(Z)-Selective Wittig and Corey-Chaykovsky reactions of propargyl ylides using trialkylgallium bases

Yoshio Nishimura, Takao Shiraishi, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Trialkylgalliums deprotonated propargylphosphonium salts and propargylsulfonium salts to form propargyl ylides. The resulted organogallium intermediates underwent the Wittig reaction and the Corey-Chaykovsky reaction with aldehydes giving (Z)-enynes and (Z)-epoxides predominantly. The use of an appropriate trialkylgallium is essential for the stereoselectivity.

Original languageEnglish
Pages (from-to)3492-3495
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number21
DOIs
Publication statusPublished - 2008 May 19

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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