Tetrahedron

Conjugate addition of nitroalkanes to dimethyl maleate. Regioselective formation of both monoesters of 2-alkylsuccinic acids

R Ballini, G Bosica, A Palmieri, M Petrini, C Pierantozzi

Index: Ballini, Roberto; Bosica, Giovanna; Palmieri, Alessandro; Petrini, Marino; Pierantozzi, Claudio Tetrahedron, 2003 , vol. 59, # 37 p. 7283 - 7289

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Citation Number: 15

Abstract

Diesters of (E)-2-alkylidenesuccinic acids obtained by conjugate addition of nitroalkanes to dimethyl maleate can be selectively monohydrolyzed at the more reactive carboxyl group to the corresponding half-ester. Alternatively, total hydrolysis to the diacid allows a subsequent selective methyl esterification of the alkanoic carboxyl group to give the other regioisomeric half-ester. 2-Alkylsuccinic monoesters can be finally obtained by catalytic hydrogenation ...