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Organocatalytic Sigmatropic Reactions: Development of a [2,3] Wittig Rearrangement through Secondary Amine Catalysis

Andrew McNally, Brian Evans, Matthew J. Gaunt*

*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK, Email: mjg32cam.ac.uk

A. McNally, B. Evans, M. J. Gaunt, Angew. Chem. Int. Ed., 2006, 45, 2116-2119.

DOI: 10.1002/anie.200504301 (free Supporting Information)


Abstract

An organocatalytic [2,3] Wittig rearrangement through secondary amine catalysis displays a broad substrate scope and proceeds with good diastereoselectivity. The reaction conditions are remarkably mild, and the transformation is simple to perform. A chiral pyrrolidine was identified, that effects an organocatalytic enantioselective simatropic rearrangement.

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proposed mechanism



Key Words

[2,3]-Wittig Rearrangement, asymmetric synthesis, enantioselectivity, organocatalysis, sigmatropic rearrangements


ID: J06-Y2006-3780