Título Atroposelective Transfer Hydrogenation of Biaryl Aminals via Dynamic Kinetic Resolution. Synthesis of Axially Chiral Diamines
Autores CARMONA CARMONA, JOSÉ ALBERTO, Rodriguez-Franco, Carlos , Lopez-Serrano, Joaquin , Ros, Abel , Iglesias-Siguenza, Javier , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin
Publicación externa Si
Medio ACS Catal.
Alcance Article
Naturaleza Científica
Cuartil JCR 1
Cuartil SJR 1
Impacto JCR 13.7
Impacto SJR 4.202
Fecha de publicacion 02/04/2021
ISI 000637003700032
DOI 10.1021/acscatal.1c00571
Abstract An efficient dynamic kinetic resolution (DKR) approach for the synthesis of axially chiral diamines has been developed on the basis of a ruthenium-catalyzed enantioselective transfer hydrogenation. The strategy relies on the configurational instability of cyclic biaryl aminal precursors in equilibrium with their amino-imine open forms, as supported by DFT calculations. This protocol features a broad substrate scope of aliphatic amines and biaryl scaffolds and proceeds under very mild conditions, allowing the preparation of BINAM homologues in good to high yields and nearly perfect enantioselectivities (up to 99% ee).
Palabras clave asymmetric catalysis; dynamic kinetic resolution; transfer hydrogenation; axial chirality; diamines
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