Rhodium-catalyzed enantioselective transfer hydrogenation of α-chloro β-ketophosphonates <i>via</i> dynamic kinetic resolution

A rhodium-catalyzed asymmetric transfer hydrogenation (ATH) of α-chloro β-ketophosphonates <i>via</i> 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.

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Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc00367a
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

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

Gen‐Qiang Chen, Xiaobing Ding, Long‐Sheng Zheng, Xumu Zhang et al.
Chemical Communications
Asymmetric Hydrogenation and Catalysis
article

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

Gen‐Qiang Chen, Xiaobing Ding, Long‐Sheng Zheng, Xumu Zhang, Virginie Ratovelomanana‐Vidal, Sai Ruan, Cheng Wang
article en

Abstract

A rhodium-catalyzed asymmetric transfer hydrogenation (ATH) of α-chloro β-ketophosphonates <i>via</i> 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.

Chemical CommunicationsVol. 61(61)
Centre National de la Recherche Scientifique (FR), Chimie ParisTech - PSL (FR), Université Paris Sciences et Lettres (FR), Southern University of Science and Technology (CN)
National Natural Science Foundation of China, Science, Technology and Innovation Commission of Shenzhen Municipality, Basic and Applied Basic Research Foundation of Guangdong Province
Openalex Percentile: Top 88%
Asymmetric Hydrogenation and Catalysis
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