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Practical synthesis of enantiopure benzylamines by catalytic hydrogenation or transfer hydrogenation reactions in isopropanol using a Ru-pybox catalyst

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Abstract

The screening of a family of complexes of the formula [RuCl2(R-pybox)(L)] (R-pybox = Ph-, iPr- or indane-pybox; L = monodentate P, N or C ligand) in the enantioselective hydrogenation of N-aryl imines indicates a strong influence of the R-pybox substituents and the L ligand in the process. A comparison indicates that the best results are obtained with the complex [RuCl2(Ph-pybox)(PPh(OMe)2)] which provided values of 99% ee for the reduction of several imines derived from aryl alkyl ketones. It is worth noting that this complex is capable of reducing the mentioned imines under transfer hydrogenation conditions using isopropanol as a hydrogen donor with equally high enantioselectivities.

Graphical abstract: Practical synthesis of enantiopure benzylamines by catalytic hydrogenation or transfer hydrogenation reactions in isopropanol using a Ru-pybox catalyst

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Publication details

The article was received on 04 Oct 2017, accepted on 30 Nov 2017 and first published on 01 Dec 2017


Article type: Research Article
DOI: 10.1039/C7QO00908A
Citation: Org. Chem. Front., 2018, Advance Article
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    Practical synthesis of enantiopure benzylamines by catalytic hydrogenation or transfer hydrogenation reactions in isopropanol using a Ru-pybox catalyst

    E. de Julián, E. Menéndez-Pedregal, M. Claros, M. Vaquero, J. Díez, E. Lastra, P. Gamasa and A. Pizzano, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00908A

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