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Synthesis 1996; 1996(6): 707-710
DOI: 10.1055/s-1996-4278
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Phosphoryl Functionalized Bishomoallyl Alcohols by Ring Opening of Epoxides with Lithiated Allyldiphenylphosphane Oxide

Jens-Kerim Ergüden, Ernst Schaumann*
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany, Fax +49(5323)722858; e-mail: schaumann@ioc.tu-clausthal.de
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Publication Date:
31 December 2000 (online)

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Epoxides are attacked by the lithiated anion of allyldiphenylphosphane oxide in 1,2-dimethoxyethane as solvent in a boron trifluoride-diethyl ether complex promoted ring opening reaction to afford a mixture of regioisomeric bishomoallyl alcohols (α- and γ-attack of the nucleophile) in good overall yields. When toluene is used as reaction medium a pronounced preference for γ-attack of the anion is observed.

allylphosphane oxides - carbanion - epoxides - alken-5-ols - solvent effect