Journal of organometallic chemistry

Palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-, benzothiophene-and indole-based substrates by dimethyl malonate anion

G Primault, JY Legros, JC Fiaud

Index: Primault, Gaelle; Legros, Jean-Yves; Fiaud, Jean-Claude Journal of Organometallic Chemistry, 2003 , vol. 687, # 2 p. 353 - 364

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Citation Number: 16

Abstract

The palladium-catalyzed benzylic-like nucleophilic substitution of acetates derived from benzofuran, benzothiophene and indole was investigated. The asymmetric substitution on racemic 1-(2-benzofuryl) ethyl acetate gave disappointing results, but the substitution product was obtained in 98% ee from (S)-1-(2-benzofuryl) ethyl acetate with overall retention of configuration.