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Synthesis 1990; 1990(2): 109-111
DOI: 10.1055/s-1990-26801
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Novel ortho-Alkoxy-Substituted Phosphorus Ylides and Their Stereoselectivity in Witting Reactions

Suruliappa Jeganathan* , Masamitsu Tsukarmoto, Manfred Schlosser
  • *Institut de Chimie organique de l'Université, Rue de la Barre 2, CH-1005 Lausanne, Switzerland
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Publication Date:
17 September 2002 (online)

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The stereochemistry of the reactions between tris(2-methoxy-methoxyphenyl)phosphonioethanide (1f), -butanide (2f), and -phenyl-methanide (3f) and a variety of aldehydes was investigated. Ylides having a β-unbranched aliphatic sidechain, such as 2f, and saturated straight-chain aldehydes give olefins with unprecedented cis-selectivity (cis/trans ≍ 200:1).