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Synlett 1993; 1993(2): 125-126
DOI: 10.1055/s-1993-22372
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Improved cis Selectivities of Carbonyl Substituted, Stable Phosphorus Ylids

Vijay Patil* , Manfred Schlosser
  • *Institut de Chimie organique de l'Université, Rue de la Barre 2, CH-1005 Lausanne, Switzerland
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Publication History

Publication Date:
19 March 2002 (online)

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Tris(2-methoxymethoxyphenyl)phosphine was readily quarternized when treated with methyl bromoacetate. The resulting phosphonium salt was deprotonated to give the corresponding ylid. The latter intermediate reacted with saturated, unsaturated or α-alkoxy substituted aliphatic aldehydes to produce α,β-unsaturated esters with moderate to excellent cis selectivity when methanol was used as the solvent.

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