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, Steven M. Toms

Research output: Contribution to journalArticlepeer-review

59 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5437-5440
Number of pages4
JournalOrganic Letters
Volume10
Issue number23
DOIs
Publication statusPublished - 4 Dec 2008

Keywords

  • LATENT ALDEHYDE EQUIVALENTS
  • BETA-AMINO ACIDS
  • ASYMMETRIC-SYNTHESIS
  • ETHYL (DIARYLPHOSPHONO)ACETATES
  • OLEFINATION REACTION
  • CARBONYL-COMPOUNDS
  • ESTERS
  • LITHIUM
  • CONSTRUCTION
  • DERIVATIVES

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