Highly Efficient Asymmetric Hydrogenation of 2-Methylenesuccinamic Acid Using a Rh-DuPHOS Catalyst

An extremely efficient route to highly enantiomerically enriched 2-methylsuccinamic acid via asymmetric hydrogenation has been developed. By using [(S,S)-Et-DuPHOS Rh COD]BF4 as the precatalyst under a set of broadly optimised process parameters, (R)-2-methylsuccinamic acid was obtained in 96% ee at...

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Bibliographic Details
Published in:Organic process research & development 2003-05, Vol.7 (3), p.407-411
Main Authors: Cobley, Christopher J, Lennon, Ian C, Praquin, Céline, Zanotti-Gerosa, Antonio, Appell, Robert B, Goralski, Christian T, Sutterer, Angela C
Format: Article
Language:English
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Summary:An extremely efficient route to highly enantiomerically enriched 2-methylsuccinamic acid via asymmetric hydrogenation has been developed. By using [(S,S)-Et-DuPHOS Rh COD]BF4 as the precatalyst under a set of broadly optimised process parameters, (R)-2-methylsuccinamic acid was obtained in 96% ee at a substrate-to-catalyst ratio (S/C) of 100000 (average turnover frequency ∼13000 h-1). The exclusion of chloride-containing contaminants in the substrate was found to be crucial in obtaining exceptionally low catalyst loadings. This material could be upgraded with a single-crystal digestion to yield (R)-2-methylsuccinamic acid in >99.5% ee containing less than 1 ppm rhodium.
ISSN:1083-6160
1520-586X
DOI:10.1021/op0256183