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Synlett 1996; 1996(12): 1195-1196
DOI: 10.1055/s-1996-5700
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2-Alkenyldiphenylphosphine Oxides and PO-Ylids Derived Thereof in trans Selective Horner-Wittig Olefination Reactions

Rong-qiang Liu, Manfred Schlosser*
  • *Institut de Chemie organique de l’Université, Bâtiment de Chemie (BCh), CH-1015 Lausanne-Dorigny, Switzerland, Fax +41(21)6923965
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Publication Date:
31 December 2000 (online)

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Allylic PO-ylids generated by deprotonation of 2-alkenyldiphenylphosphine oxides with butyllithium can be used to prepare 1,3-dienes trans-selectively. The (Z/E) ratios of the newly formed double bond are 1 : 99 when straight-chain, while they range from 2 : 98 to 4 : 96 when β-branched aliphatic, and from 4 : 96 to 6 : 94 when aromatic aldehydes are employed.

allyl type phosphine oxides - dienes - trans stereoselectivity - Horner olefination reactions - PO-ylids