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: mjg32
cam.ac.uk
A. McNally, B. Evans, M. J. Gaunt, Angew. Chem. Int. Ed., 2006, 45, 2116-2119.
DOI: 10.1002/anie.200504301
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
