Synthesis of cyclopent-2-enones through stepwise [3 + 2] cycloaddition of simple silyl enol ethers and alk-1-ynes

Masahiko Yamaguchi, Michiru Sehata, Akio Hayashi, Masahiro Hirama

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Treatment of silyl enol ethers and alk-1-ynes with SnCl4-Bu 3N reagent followed by DBU, leads to cyclopent-2-enones, through [3 + 2] cycloaddition reactions; the initial carbon-carbon bond formation is carbometallation of alkynes, and the second step is a base-promoted intramolecular alkylation which reductively eliminates tin species (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene).

Original languageEnglish
Pages (from-to)1708-1709
Number of pages2
JournalJournal of the Chemical Society, Chemical Communications
Issue number22
DOIs
Publication statusPublished - 1993 Dec 1

ASJC Scopus subject areas

  • Molecular Medicine

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