An Efficient Method for Cyclopentene Annulation onto α,β-Unsaturated Ketones: W(CO)5(L)-Catalyzed 5-Endo-Dig Cyclization of 6-Siloxy-5-en-1-ynes

Nobuharu Iwasawa, Tomoya Miura, Koichi Kiyota, Hiroyuki Kusama, Kooyeon Lee, Phil Ho Lee

Research output: Contribution to journalArticlepeer-review

89 Citations (Scopus)

Abstract

(Matrix Presented) A highly efficient method for the cyclopentene annulation onto α,β-unsaturated ketones is described. Indium-mediated 1,4-propargylation onto α,β-unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives the 6-siloxy-5-en-1-yne derivatives, which undergo W(CO)5(L)-catalyzed 5-endo-dig cyclization to give the corresponding cyclopentene derivatives in good yield.

Original languageEnglish
Pages (from-to)4463-4466
Number of pages4
JournalOrganic Letters
Volume4
Issue number25
DOIs
Publication statusPublished - Dec 12 2002
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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