CARMONA CARMONA, JOSÉ ALBERTO, Rodriguez-Franco, Carlos , Lopez-Serrano, Joaquin , Ros, Abel , Iglesias-Siguenza, Javier , Fernandez, Rosario , Lassaletta, Jose M. , Hornillos, Valentin
Si
ACS Catal
Article
Científica
13.7
4.202
02/04/2021
000637003700032
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).
asymmetric catalysis; dynamic kinetic resolution; transfer hydrogenation; axial chirality; diamines