W(CO)5(L)-catalyzed formal Cope rearrangement of allenyl silyl enol ethers

Tomoya Miura, Koichi Kiyota, Hiroyuki Kusama, Nobuharu Iwasawa

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

(Chemical Equation Presented) On treatment of 5-siloxyhexa-1,2,5-trienes with a catalytic amount of W(CO)6 under photoirradiation, formal Cope rearrangement proceeded to give 2-siloxyhex-1-en-5-ynes in good yield. The electrophilic activation of the allenyl moiety by W(CO)5 triggers the intramolecular attack of the silyl enol ether in a 6-endo manner to produce a cyclohexenyl tungsten species. Carbon-carbon bond cleavage occurs by electron donation from the anionic W(CO)5 into the silyloxonium moiety to afford the products with regeneration of the W(CO)5(L).

Original languageEnglish
Pages (from-to)1445-1447
Number of pages3
JournalOrganic Letters
Volume7
Issue number8
DOIs
Publication statusPublished - Apr 14 2005
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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