The first addition of silyl enol ethers to internal unactivated alkynes

Ken Ichiro Imamura, Eiji Yoshikawa, Vladimir Gevorgyan, Yoshinori Yamamoto

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

The EtAlCl2-mediated intramolecular addition of silyl enol ethers to both terminal and internal unactivated alkynes, bearing alkyl and phenyl susbstituents at the alkyne moiety, proceeded exclusively in the endo- fashion to give mono- and bicyclic β,γ-unsaturated ketones in good to excellent yields. The mechanism of this regiospecific Lewis acid-assisted carbocyclization is proposed.

Original languageEnglish (US)
Pages (from-to)4081-4084
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number21
DOIs
StatePublished - May 21 1999
Externally publishedYes

Keywords

  • Alkynes
  • Carbocyclization
  • Lewis acid
  • Silyl enol ethers

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The first addition of silyl enol ethers to internal unactivated alkynes'. Together they form a unique fingerprint.

Cite this