Tetrahedron

Formation of dihydroxyselenides from allylic alcohols and their conversion to β-hydroxy epoxides via substitution of a phenylselenonyl group

MA Cooper, AD Ward

Index: Cooper, Matthew A.; Ward, A. David Tetrahedron, 2004 , vol. 60, # 36 p. 7963 - 7972

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Citation Number: 11

Abstract

Hydroxyselenation of allylic alcohols occurs with high regio-and stereoselectivity to give β, β′-dihydroxyphenylselanyl adducts in high yields. An exception is the reaction of the terminal alcohol, 2-methylprop-2-en-1-ol, which forms only a 1, 2-diol product. Generally, the addition is Markovnikov in orientation, but the fact that one anti-Markovnikov addition is observed and that addition to 1, 2-disubstituted alkenes shows a strong preference for one ...