Highly regioselective synthesis of cyclic enol silyl ethers using ring-closing metathesis

Akihiro Okada, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

Abstract

We developed the first highly regioselective synthesis of cyclic enol ethers from readily accessible acyclic alkenyl ketones or acyclic alkenyl silyl esters using ring-closing metathesis (RCM). The RCM of acyclic enol silyl ethers was examined using Tebbe reagent 5 or Grubbs catalyst 6 or 7 and successfully proceeded using the second generation Grubbs catalyst 7 to afford the corresponding cyclic enol ethers in high yield (up to 99%, two steps from alkenyl kenone). This process can be applied to syntheses of a variety of cyclic enol ethers in a highly regioselective manner.

Original languageEnglish
Pages (from-to)8023-8027
Number of pages5
JournalTetrahedron Letters
Volume42
Issue number45
DOIs
Publication statusPublished - Nov 5 2001
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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