Homogeneous palladium-catalyzed enantioselective hydrogenation of 5- methylenhydantoin for the synthesis of L-Valine
Résumé
In this article, we present the development of a synthetic methodology based on homogeneous catalysis for the preparation of enantioenriched L-Valine aminoacid. The enantioselective hydrogenation of 5-methylenhydantoin has been developed through broad screenings of chiral ligands, metal precursors and reaction conditions including scale-up experiments and recyclability studies. A palladium catalyzed asymmetric hydrogenation of 5-methylenhydantoin afforded the corresponding hydrogenated product in a 70 % enantiomeric excess using a substrate/catalyst ratio of 500/1. A partial racemization was observed upon hydrolysis and recovery of L-Valine.- Corresponding authors. Tel.: +33 (0)3 68 85 27 97; cmichon@unistra.fr and +33 (0)3 20 43 68 63; francine.niedercorn@univ-lille.fr
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