Work

Kinetic resolution of dihydroquinolines via Ru( II )‐ TsDPEN ‐catalyzed asymmetric transfer hydrogenation

Year: 2025

Type: article

Abstract: The kinetic resolution of 2‐substituted tetrahydro‐4‐quinolone derivatives ( N ‐tosyl azaflavones) has been accomplished by Ru(II)‐TsDPEN‐catalyzed asymmetric transfer hydrogenation (ATH). Employing HCO 2 Na in the presence of a phase transfer catalyst as the hydrogen source, this methodology proceeds under mild and operationally convenient conditions. The process provides access to enantiomerically enriched 2‐substituted‐ N ‐tosyl‐2,3‐dihydroquinolin‐4(1H)‐ones with excellent levels of enantioselectivity, frequently exceeding 99% ee. In parallel, the corresponding 2‐substituted‐1‐tosyl‐1,2,3,4‐tetrahydroquinolin‐4‐ols are obtained in high conversion, also with superior enantioselectivity up to >99% ee. Both product classes are of considerable synthetic utility, and the high selectivity factors observed underscore the efficiency of this ATH approach. Overall, these results demonstrate the value of Ru(II)‐TsDPEN catalysis combined with HCO 2 Na/PTC as a practical strategy for the enantioselective synthesis of structurally diverse azaflavone derivatives.

Source: Bulletin of the Korean Chemical Society

DOI: 10.1002/bkcs.70073

Authors: Suh Young Yu, Jihye Lee, Aimin Zhang, Jimin Kim

Institution: Chonnam National University

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Research Foundation, National Research Foundation of Korea

Awards: G1639689472, G2793326103, G6050962997