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Issue 30, 2017
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Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides

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Abstract

Asymmetric hydrogenation of various 3-substituted maleic anhydrides catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) under mild conditions was successfully developed. A wide range of 3-alkyl and 3-aryl maleic anhydrides were hydrogenated well to provide the desired products 3-substituted succinic anhydrides in one hour with excellent results (full conversions, up to 99% yield, 99% ee, 3000 TON). Importantly, we developed a creative and efficient synthetic route to construct the key intermediate of the hypoglycemic drug mitiglinide through our catalytic system.

Graphical abstract: Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides

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Publication details

The article was received on 02 Mar 2017, accepted on 20 Mar 2017 and first published on 20 Mar 2017


Article type: Communication
DOI: 10.1039/C7CC01626C
Citation: Chem. Commun., 2017,53, 4226-4229
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    Asymmetric hydrogenation of maleic anhydrides catalyzed by Rh/bisphosphine-thiourea: efficient construction of chiral succinic anhydrides

    Z. Han, R. Wang, G. Gu, X. Dong and X. Zhang, Chem. Commun., 2017, 53, 4226
    DOI: 10.1039/C7CC01626C

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