Issue 5, 2018
From the journal:

Organic Chemistry Frontiers

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

E. de Julián,a   E. Menéndez-Pedregal,a   M. Claros,a   M. Vaquero, ORCID logo b   J. Díez,a   E. Lastra, ORCID logo a   P. Gamasa*a  and  A. Pizzano ORCID logo *b  

* Corresponding authors

a Laboratorio de Compuestos Organometálicos y Catálisis (Unidad Asociada al CSIC), Departamento de Química Orgánica e Inorgánica, Instituto de Química Organometálica “Enrique Moles”, Universidad de Oviedo, 33006 Oviedo, Spain
E-mail: pgb@uniovi.es

b Instituto de Investigaciones Químicas (IIQ) and Centro de Innovación en Química Avanzada (ORFEO-CINQA), CSIC and Universidad de Sevilla, Américo Vespucio 49, 41092 Sevilla, Spain
E-mail: pizzano@iiq.csic.es

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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Article information

DOI
https://doi.org/10.1039/C7QO00908A
Article type
Research Article
Submitted
04 Oct 2017
Accepted
30 Nov 2017
First published
01 Dec 2017

Org. Chem. Front., 2018,5, 841-849

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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, 5, 841 DOI: 10.1039/C7QO00908A

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