W(CO)5(L)-catalyzed 6-endo-selective cyclization and formal Cope rearrangement of allenyl silyl enol ethers

Tomoya Miura, Koichi Kiyota, Hiroyuki Kusama, Nobuharu Iwasawa

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

On treatment of 5-siloxy-1,2,5-trienes with a catalytic amount of W(CO)6 under photoirradiation, two types of synthetically useful compounds, that is, 6-endo-cyclized products or formal Cope rearrangement products, are obtained selectively via the same intermediates simply by changing reaction conditions. In these reactions, electrophilic activation of the allene moiety is effectively achieved by coordination of W(CO)5, allowing intramolecular attack by neutral carbon nucleophiles in a 6-endo manner.

Original languageEnglish
Pages (from-to)562-568
Number of pages7
JournalJournal of Organometallic Chemistry
Volume692
Issue number1-3
DOIs
Publication statusPublished - Jan 1 2007
Externally publishedYes

Keywords

  • Allene
  • Cope rearrangement
  • Cyclization
  • Electrophilic activation
  • Tungsten

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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