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)
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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