Organic Chemistry Portal

Abstracts

Search:

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

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, Email: xweirdg.boehringer-ingelheim.com

X. Wei, J. C. Lorenz, S. Kapadia, A. Saha, N. Haddad, C. A. Busacca, C. H. Senanayake, J. Org. Chem., 2007, 72, 4250-4253.

DOI: 10.1021/jo062548f (free Supporting Information)



see article for more reactions

Abstract

A sequential allyl vinyl ether formation-Claisen rearrangement process catalyzed by a palladium(II)-phenanthroline complex 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 kilogram scale.

see article for more examples



Key Words

Claisen Rearrangement, Aldehydes, Allylation


ID: J42-Y2007-1670