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Issue 5, 2011
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Organocatalytic asymmetric transfer hydrogenation of imines

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Abstract

The asymmetric organocatalytic transfer hydrogenation of imines can be accomplished in good yields with high enantioselectivities through the use of BINOL-derived phosphoric acids as catalysts and Hantzsch esters or benzothiazoles as the hydride source. The same method can also be applied to the enantioselective reduction of benzo-fused heterocycles, such as quinolines, benzoxazines, benzothiazines, benzoxazinones, quinoxalines, quinoxalinones and a limited number of pyridines containing electron-withdrawing groups. Cascade reactions involving multiple reductions and rearrangements have been reported as well as combinations of metal-catalysed reactions, such as gold-catalyzed hydroaminations of alkynes combined with the reduction of the ensuing enamine. Although turnover frequencies of the organocatalytic imine hydrogenations are still lower than those of metal-catalyzed hydrogenations, there are several advantages. Mild and environmentally friendly conditions as well as excellent selectivity make this method a valuable approach to enantiopure amine building blocks.

Graphical abstract: Organocatalytic asymmetric transfer hydrogenation of imines

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Publication details

The article was received on 09 Feb 2011, accepted on 28 Mar 2011 and first published on 28 Apr 2011


Article type: Minireview
DOI: 10.1039/C1CY00050K
Catal. Sci. Technol., 2011,1, 727-735

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    Organocatalytic asymmetric transfer hydrogenation of imines

    J. G. de Vries and N. Mršić, Catal. Sci. Technol., 2011, 1, 727
    DOI: 10.1039/C1CY00050K

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