Atroposelective Transfer Hydrogenation of Biaryl Aminals via Dynamic Kinetic Resolution. Synthesis of Axially Chiral Diamines

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 equilibri...

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Bibliographic Details
Authors: Carmona, José A., Rodríguez Franco, Carlos, López Serrano, Joaquín, Ros Lao, Abel, Iglesias Sigüenza, Francisco Javier, Fernández Fernández, Rosario, Lassaletta, José M., Hornillos, Valentín
Format: article
Status:Published version
Publication Date:2021
Country:España
Institution:Universidad de Sevilla (US)
Repository:idUS. Depósito de Investigación de la Universidad de Sevilla
OAI Identifier:oai:idus.us.es:11441/165967
Online Access:https://hdl.handle.net/11441/165967
https://doi.org/10.1021/acscatal.1c00571
Access Level:Open access
Keyword:Asymmetric catalysis
Axial chirality
Diamines
Dynamic kinetic resolution
Transfer hydrogenation
Description
Summary: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).

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