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Rhodium-mediated asymmetric transfer hydrogenation: a diastereo- and enantioselective synthesis of syn-α-amido β-hydroxy esters

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Abstract

The preparation of syn α-benzoylamido β-hydroxy esters through asymmetric transfer hydrogenation (ATH) with a tethered Rh(III)–DPEN complex via dynamic kinetic resolution (DKR) has been developed for the first time starting from α-benzoylamido β-keto esters. A variety of α-benzoylamido β-keto esters were converted under mild conditions into the corresponding syn α-benzoylamino β-hydroxy esters with high yields (up to 98%) and diastereomeric ratios (up to >99 : 1 dr) as well as excellent enantioselectivities (up to >99% ee).

Graphical abstract: Rhodium-mediated asymmetric transfer hydrogenation: a diastereo- and enantioselective synthesis of syn-α-amido β-hydroxy esters

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Publication details

The article was received on 25 Oct 2017, accepted on 07 Dec 2017 and first published on 07 Dec 2017


Article type: Communication
DOI: 10.1039/C7CC08231B
Citation: Chem. Commun., 2018, Advance Article
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    Rhodium-mediated asymmetric transfer hydrogenation: a diastereo- and enantioselective synthesis of syn-α-amido β-hydroxy esters

    L. Zheng, C. Férard, P. Phansavath and V. Ratovelomanana-Vidal, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC08231B

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