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

✍ Scribed by Roberto Ballini; Giovanna Bosica; Alessandro Palmieri; Marino Petrini; Claudio Pierantozzi

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 131 KB
• Volume: 59
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(03)01175-x

✦ Synopsis

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 of the unsaturated derivatives.