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Tandem Pd(II)-Catalyzed Vinyl Ether Exchange−Claisen Rearrangement as a Facile Approach to γ,δ-Unsaturated Aldehydes

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Xudong Wei,* Jon C. Lorenz, Suresh Kapadia, Anjan Saha, Nizar Haddad, Carl A. Busacca, and Chris H. Senanayake

Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, Connecticut 06877 xwei@rdg.boehringer-ingelheim.com

J. Org. Chem., 2007, 72 (11), pp 4250–4253

DOI: 10.1021/jo062548f

Publication Date (Web): April 21, 2007

Section:

Aliphatic Compounds

Abstract

A sequential allyl vinyl ether formation−Claisen rearrangement process catalyzed by a palladium(II)−phenanthroline complex is reported. The effects of allylic alcohol structure, type of vinylating agent, and palladium catalysts are discussed. This method provides a convenient approach to γ,δ-unsaturated aldehydes under mild conditions that avoid the use of toxic Hg(II) catalysts. The new methodology has been successfully demonstrated on the kilogram scale.

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

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Stereoselective Synthesis of (+)-Euphococcinine and (−)-Adaline
Mélissa Arbour, Stéphanie Roy, Cédrickx Godbout and Claude Spino
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