Tetrahedron Letters

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

A Okada, T Ohshima, M Shibasaki

Index: Okada, Akihiro; Ohshima, Takashi; Shibasaki, Masakatsu Tetrahedron Letters, 2001 , vol. 42, # 45 p. 8023 - 8027

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Citation Number: 58

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 ...