Rhodium-catalyzed enantioselective transfer hydrogenation of α-chloro β-ketophosphonates via dynamic kinetic resolution

Jun Wang; Xiaobing Ding; Sai Ruan; Longsheng Zheng; Virginie Ratovelomanana-Vidal; Gen-Qiang Chen; Xumu Zhang

doi:10.1039/d5cc00367a

Rhodium-catalyzed enantioselective transfer hydrogenation of α-chloro β-ketophosphonates via dynamic kinetic resolution

Chem Commun (Camb). 2025 Jun 27. doi: 10.1039/d5cc00367a. Online ahead of print.

Authors

Jun Wang^{1

2}, Xiaobing Ding¹, Sai Ruan¹, Longsheng Zheng¹, Virginie Ratovelomanana-Vidal³, Gen-Qiang Chen², Xumu Zhang¹

Affiliations

¹ Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Department of Chemistry and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen 518055, People's Republic of China. dingxb@sustech.edu.cn.
² Academy for Advanced Interdisciplinary Studies and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518000, People's Republic of China. chengq@sustech.edu.cn.
³ Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences, CSB2D team, PSL University, 75005 Paris, France. virginie.vidal@chimieparistech.psl.eu.

PMID: 40575869
DOI: 10.1039/d5cc00367a

Abstract

A rhodium-catalyzed asymmetric transfer hydrogenation (ATH) of α-chloro β-ketophosphonates via dynamic kinetic resolution (DKR) has been developed. A wide range of syn α-chloro β-hydroxyphosphonates were efficiently synthesized with high yields and excellent enantio- and diastereoselectivities (up to 99% ee and > 99 : 1 dr) under mild reaction conditions. A gram-scale experiment was conducted successfully, which offers a straightforward approach to a key intermediate of fosfomycin.