Sulfinamide Phosphinates as Chiral Catalysts for the Enantioselective Organocatalytic Reduction of Imines.
A new type of chiral sulfinamide phosphinate catalysts with up to three stereogenic centers, readily accessible from commercially available starting materials, is reported. The naphthyl derivative SulPhos proved to be highly efficient in the organocatalytic asymmetric imine reduction, leading to a wide range of arylmethylamines in high yields with up to 99% ee under 10% catalyst loading. The synthetic utility of this method was demonstrated by the expeditious enantioselective synthesis of the calcimimetic NPS-R568.
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla , C/Profesor García González, 2, 41012 Seville, Spain.
Ahmed
A
Chelouan
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla , C/Profesor García González, 2, 41012 Seville, Spain.
Rocío
R
Recio
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla , C/Profesor García González, 2, 41012 Seville, Spain.
Lorenzo G
LG
Borrego
Asymmetric Synthesis and Functional Nanosystem Group, CSIC-University of Seville , C/Américo Vespucio, 49. Isla de la Cartuja, 41092 Seville, Spain.
Eleuterio
E
Álvarez
Asymmetric Synthesis and Functional Nanosystem Group, CSIC-University of Seville , C/Américo Vespucio, 49. Isla de la Cartuja, 41092 Seville, Spain.
Noureddine
N
Khiar
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla , C/Profesor García González, 2, 41012 Seville, Spain.
Inmaculada
I
Fernández