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.davies
chem.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
