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J Am Chem Soc. 2018 Nov 29. doi: 10.1021/jacs.8b11547. [Epub ahead of print]

Direct Asymmetric Hydrogenation of N-Methyl and N-Alkyl Imines with an Ir(III)H Catalyst.

Author information

1
Institute for Research in Biomedicine (IRB Barcelona), Barcelona Institute of Science and Technology , Baldiri Reixac 10 , 08028 Barcelona , Spain.
2
Dept. Química Inorgànica i Orgànica , Universitat de Barcelona , Martí i Franquès 1 , 08028 Barcelona , Spain.
3
Dept. de Química, Ed. C.n. , Universitat Autònoma de Barcelona , Cerdanyola del Vallès , Barcelona 08193 , Spain.
4
Dipt. di Chimica e Farmacia , Università di Sassari , via Vienna 2 , I-07017 Sassari , Italy.

Abstract

A novel cationic [IrH(THF)(P,N)(imine)] [BArF] catalyst containing a P-stereogenic MaxPHOX ligand is described for the direct asymmetric hydrogenation of N-methyl and N-alkyl imines. This is the first catalytic system to attain high enantioselectivity (up to 94% ee) in this type of transformation. The labile tetrahydrofuran ligand allows for effective activation and reactivity, even at low temperatures. Density functional theory calculations allowed the rationalization of the stereochemical course of the reaction.

PMID:
30475609
DOI:
10.1021/jacs.8b11547

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