Diastereoselective allylations of allyl-propargyl hybrid cations: Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers

Teruhiko Ishikawa, Toshiaki Aikawa, Yumiko Mori, Seiki Saito

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Chiral C(4)-substituted (E)- or (Z)-1-alkynyl-1-trimethylsilyloxy-2-butene systems provide anti-(Z) or syn-(Z) conjugated dienyne, with a very high level of stereocontrol, on treatment with BF3·OEt2 in CH2Cl2 at -50°C in the presence of allyltrimethylsilane. The Cieplak conformation for (Z)-substrates and neighboring-group participation for (2)-substrates are considered to be responsible for the stereochemical consequences.

Original languageEnglish
Pages (from-to)1369-1372
Number of pages4
JournalOrganic Letters
Volume6
Issue number9
DOIs
Publication statusPublished - Apr 29 2004

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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