Highly (E)-selective Wadsworth-Emmons reactions promoted by methylmagnesium bromide

Org Lett. 2008 Dec 4;10(23):5437-40. doi: 10.1021/ol802212e.

Abstract

An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmons reaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.