Issue 11, 2021

Kinetic resolution of 2-aryl-2,3-dihydroquinolin-4(1H)-one derivatives by rhodium-catalysed asymmetric transfer hydrogenation

Abstract

The kinetic resolution of 2-aryl tetrahydro-4-quinolone derivatives was efficiently achieved by rhodium-catalysed asymmetric transfer hydrogenation using HCO2H/DABCO as the hydrogen source. The reaction afforded the enantiomerically enriched 2-aryl-2,3-dihydroquinolin-4(1H)-ones with excellent levels of enantioselectivity (up to >99% ee) as well as the corresponding synthetically useful enantiomerically enriched 2-aryl tetrahydro-4-quinolols in high isolated yields and up to >99% enantioselectivity with high selectivity factors (s up to 1057).

Graphical abstract: Kinetic resolution of 2-aryl-2,3-dihydroquinolin-4(1H)-one derivatives by rhodium-catalysed asymmetric transfer hydrogenation

Supplementary files

Article information

Article type
Research Article
Submitted
25 Jan 2021
Accepted
19 Mar 2021
First published
26 Mar 2021

Org. Chem. Front., 2021,8, 2504-2509

Kinetic resolution of 2-aryl-2,3-dihydroquinolin-4(1H)-one derivatives by rhodium-catalysed asymmetric transfer hydrogenation

B. He, P. Phansavath and V. Ratovelomanana-Vidal, Org. Chem. Front., 2021, 8, 2504 DOI: 10.1039/D1QO00141H

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