Homogeneous palladium-catalyzed enantioselective hydrogenation of 5-methylenhydantoin for the synthesis of L-Valine

•The enantioselective hydrogenation of 5-methylenhydantoin can lead to L-Valine.•A palladium catalyst allowed the asymmetric hydrogenation of 5-methylenhydantoin.•Hydrolysis of the corresponding hydrogenated product afforded L-Valine.•A partial racemization was observed upon hydrolysis and recovery...

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Published inJournal of organometallic chemistry Vol. 929; p. 121572
Main Authors Hayouni, Safa, Michon, Christophe, Morvan, Didier, Bellière-Baca, Virginie, Agbossou-Niedercorn, Francine
Format Journal Article
LanguageEnglish
Published Elsevier B.V 14.12.2020
Elsevier
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Summary:•The enantioselective hydrogenation of 5-methylenhydantoin can lead to L-Valine.•A palladium catalyst allowed the asymmetric hydrogenation of 5-methylenhydantoin.•Hydrolysis of the corresponding hydrogenated product afforded L-Valine.•A partial racemization was observed upon hydrolysis and recovery of L-Valine. 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. [Display omitted]
ISSN:0022-328X
1872-8561
0022-328X
DOI:10.1016/j.jorganchem.2020.121572