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

Akihiro Okada, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

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

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Cyclic Ethers
Ethers
Ketones
Catalysts
Esters

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Highly regioselective synthesis of cyclic enol silyl ethers using ring-closing metathesis. / Okada, Akihiro; Ohshima, Takashi; Shibasaki, Masakatsu.

In: Tetrahedron Letters, Vol. 42, No. 45, 05.11.2001, p. 8023-8027.

Research output: Contribution to journalArticle

Okada, Akihiro ; Ohshima, Takashi ; Shibasaki, Masakatsu. / Highly regioselective synthesis of cyclic enol silyl ethers using ring-closing metathesis. In: Tetrahedron Letters. 2001 ; Vol. 42, No. 45. pp. 8023-8027.
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