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Org Lett. 2007 Jul 5;9(14):2621-4. Epub 2007 Jun 19.

Highly enantioselective decarboxylative protonation of alpha-aminomalonates mediated by thiourea cinchona alkaloid derivatives: access to both enantiomers of cyclic and acyclic alpha-aminoacids.

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  • 1Laboratoire de Chimie Moléculaire et Thio-organique, ENSICAEN, Université de Caen-Basse Normandie, CNRS, 6 Boulevard du Maréchal Juin, 14050 Caen, France.

Abstract

Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer 6 derived from quinine.

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