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Highly (E)-Selective Wadsworth-Emmons Reactions Promoted by Methylmagnesium Bromide

Timothy D. W. Claridge, Stephen G. Davies*, James A. Lee, Rebecca L. Nicholson, Paul M. Roberts, Angela J. Russell, Andrew D. Smith and Steven M. Toms

*Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, U.K., Email: steve.davieschem.ox.ac.uk

T. D. W. Claridge, S. G. Davies, J. A. Lee, R. L. Nicholson, P. M. Roberts, A. J. Russel, A. D. Smith, S. M. Toms, Org. Lett., 2008, 10, 5437-5440.

DOI: 10.1021/ol802212e (free Supporting Information)


Abstract

A simple protocol for a highly E-selective Wadsworth-Emmons reaction via deprotonation of alkyl diethylphosphonoacetates with MeMgBr allows the conversion of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes.


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Key Words

Wittig-Horner Reaction, α,β-unsaturated esters


ID: J54-Y2008-3640