Regioselective SN2 opening of vinylic epoxides with trialkylzincates and trialkylaluminates

O Equey, E Vrancken, A Alexakis

Index: Equey, Olivier; Vrancken, Emmanuel; Alexakis, Alexandre European Journal of Organic Chemistry, 2004 , # 10 p. 2151 - 2159

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Citation Number: 18

Abstract

Abstract The use of trialkylorganozincates and tetraalkylaluminates allows regioselective SN 2 nucleophilic opening of vinylic epoxides. The reaction occurs with an anti-substitution pattern and can be applied to a wide range of substrates. We also show that the solvent and the structure of the epoxide have an influence on the substitution products' ratio.(© Wiley- VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)