An Improved Procedure for the Pd(II)-Catalyzed Claisen Rearrangement via In Situ Enol Ether Exchange

Masaharu Sugiura; Manabu Yanagisawa; Takeshi Nakai

doi:10.1055/s-1995-5005

Synlett 1995; 1995(5): 447-448
DOI: 10.1055/s-1995-5005

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An Improved Procedure for the Pd(II)-Catalyzed Claisen Rearrangement via In Situ Enol Ether Exchange

Masaharu Sugiura, Manabu Yanagisawa, Takeshi Nakai^*

^*Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo, Japan

Abstract

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The title rearrangement, when carried out using CF₃CO₂H as a co-catalyst, is shown to proceed at room temperature to afford the Claisen product with a high level of both diastereoselection and asymmetric transmission. The scope and limitation of the new procedure are defined.

Pd(II)-catalysis - Claisen rearrangement - enol ether exchange - diastereocontrol

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