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Issue 8, 2018
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Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives

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Abstract

An efficient, stereoselective route to 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives through an asymmetric transfer hydrogenation of ring-substituted β-amino ketones via dynamic kinetic resolution has been developed. The reaction proceeded under mild conditions in the presence of RuCl[(S,S)-TsDPEN](benzene) and HCO2H/Et3N (5 : 2) as the hydrogen source, delivering in good yields a variety of syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives with excellent enantioselectivities (up to 99% ee) and diastereomeric ratios up to 71 : 29 dr.

Graphical abstract: Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives

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Publication details

The article was received on 21 Dec 2017, accepted on 27 Feb 2018 and first published on 28 Feb 2018


Article type: Research Article
DOI: 10.1039/C7QO01142C
Citation: Org. Chem. Front., 2018,5, 1366-1370
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    Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives

    L. Zheng, P. Phansavath and V. Ratovelomanana-Vidal, Org. Chem. Front., 2018, 5, 1366
    DOI: 10.1039/C7QO01142C

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