A comparison between the two most common reduction approaches for obtaining chiral amines, asymmetric hydrogenation (AH) versus asymmetric transfer hydrogenation (ATH), was accomplished by using iridium complexes based on atropoisomeric diphosphines and cyclic diamines as ligands respectively. Seven substrates, different in electronic and steric properties, were screened applying both reduction methods. For AH the best results in terms of enantioselectivity (e.e. up to 64%) were obtained by using [Ir(COD)(TetraMe-BITIOP)]Cl in the presence of DCDMH as additive. ATH was carried out with [IrCp*(CAMPY)Cl]Cl as catalyst, allowing the obtainment of the products with appreciable e.e. (up to 76%).

Asymmetric Hydrogenation vs Transfer Hydrogenation in the Reduction of Cyclic Imines / G. Facchetti, R. Bucci, M. Fusè, I. Rimoldi. - In: CHEMISTRYSELECT. - ISSN 2365-6549. - 3:31(2018 Aug), pp. 8797-8800. [10.1002/slct.201802223]

Asymmetric Hydrogenation vs Transfer Hydrogenation in the Reduction of Cyclic Imines

Giorgio Facchetti;Raffaella Bucci;Isabella Rimoldi
2018-08

Abstract

A comparison between the two most common reduction approaches for obtaining chiral amines, asymmetric hydrogenation (AH) versus asymmetric transfer hydrogenation (ATH), was accomplished by using iridium complexes based on atropoisomeric diphosphines and cyclic diamines as ligands respectively. Seven substrates, different in electronic and steric properties, were screened applying both reduction methods. For AH the best results in terms of enantioselectivity (e.e. up to 64%) were obtained by using [Ir(COD)(TetraMe-BITIOP)]Cl in the presence of DCDMH as additive. ATH was carried out with [IrCp*(CAMPY)Cl]Cl as catalyst, allowing the obtainment of the products with appreciable e.e. (up to 76%).
asymmetric reduction; atropoisomeric diphosphines; cyclic imines; iridium complexes
Settore CHIM/03 - Chimica Generale e Inorganica
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/586789
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