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

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Bearings (structural)
Allylation
Cations
cations
butenes
Substrates
synthesis
Conformations
2-butene
allyltrimethylsilane

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Diastereoselective allylations of allyl-propargyl hybrid cations : Synthesis of conjugated 1,5-dien-7-yne frameworks bearing C(4)-stereogenic centers. / Ishikawa, Teruhiko; Aikawa, Toshiaki; Mori, Yumiko; Saito, Seiki.

In: Organic Letters, Vol. 6, No. 9, 29.04.2004, p. 1369-1372.

Research output: Contribution to journalArticle

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