W(CO)5(L)-catalyzed endo-selective cyclization of allenyl silyl enol ethers: An efficient method for the cyclopentene annulation onto α,β-unsaturated ketones

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

Research output: Contribution to journalArticlepeer-review

47 Citations (Scopus)

Abstract

(Matrix presented) Indium-mediated allenylation of α,β -unsaturated ketones in the presence of tert-butyldimethylsilyl triflate and dimethyl sulfide gives 6-siloxy-1,2,5-trienes, which undergo W(CO) 5(L)-catalyzed 5-endo cyclization to give the corresponding cyclopentene derivatives in good yield. Furthermore, this novel W(CO) 5(L)-catalyzed cyclization of allenyl silyl enol ethers proceeds in a 6-endo manner when 5-siloxy-1,2,5-trienes are employed as a substrate. In these reactions, effective electrophilic activation of allenyl compounds for attack by silyl enol ethers is achieved using a catalytic amount of W(CO) 6.

Original languageEnglish
Pages (from-to)1725-1728
Number of pages4
JournalOrganic Letters
Volume5
Issue number10
DOIs
Publication statusPublished - May 15 2003
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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