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
Published inACS catalysis Vol. 11; no. 7; pp. 4117 - 4124
Main Authors Carmona, José A, Rodríguez-Franco, Carlos, López-Serrano, Joaquín, Ros, Abel, Iglesias-Sigüenza, Javier, Fernández, Rosario, Lassaletta, José M, Hornillos, Valentín
Format Journal Article
LanguageEnglish
Published American Chemical Society 02.04.2021
Subjects
axial chirality
transfer hydrogenation
asymmetric catalysis
dynamic kinetic resolution
diamines
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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).
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.1c00571