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