Horner-Wadsworth-Emmons reaction for the synthesis of unusual α,β-didehydroamino acids with a chiral axis

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Abstract

The Horner-Wadsworth-Emmons reaction of N-benzyloxycarbonyl(dimethoxyphosphinyl) glycine esters withs-symmetric prochiral 4-substituted-cyclohexanones under basic conditions is described. This reaction gives unusual α,β-didehydroamino acids with a chiral axis in their racemic form. The methodology has been extended to the synthesis of dipeptides containing a phenylalanine residue and these unusual new α,β-didehydroamino acids at the i+2 position.

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Cativiela, C., Díaz-De-Villegas, M. D., Gálvez, J. A., & Su, G. (2004). Horner-Wadsworth-Emmons reaction for the synthesis of unusual α,β-didehydroamino acids with a chiral axis. Arkivoc, 2004(4), 59–66.

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