Pd(II)-Catalyzed enantioselective C-H olefination toward the synthesis of P-stereogenic phosphinamides

Zi-Jia Chen; Ling-Jie Fan; Pei-Pei Xie; Pu-Fan Qian; Xinquan Hu; Tao Zhou; Bing-Feng Shi

doi:10.1039/d3cc05052a

Pd(II)-Catalyzed enantioselective C-H olefination toward the synthesis of P-stereogenic phosphinamides

Chem Commun (Camb). 2024 Feb 6;60(12):1623-1626. doi: 10.1039/d3cc05052a.

Authors

Zi-Jia Chen¹, Ling-Jie Fan², Pei-Pei Xie¹, Pu-Fan Qian¹, Xinquan Hu², Tao Zhou^{1

3}, Bing-Feng Shi^{1

3

4}

Affiliations

¹ Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027, China. taozhou.zju.edu.cn.
² College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, China.
³ College of Material Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, Zhejiang, China.
⁴ College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China.

PMID: 38230709
DOI: 10.1039/d3cc05052a

Abstract

P-Stereogenic phosphorus compounds are important structural elements in chiral ligands or organocatalysts. Herein, we report a Pd(II)-catalyzed enantioselective C-H olefination toward the synthesis of P-stereogenic phosphinamides using cheap commercially available L-pGlu-OH as a chiral ligand. A broad range of P-stereogenic phosphinamides were gained in good yields with high enantioselectivities (33 examples, up to 77% yield, 99% ee) via desymmetrization and kinetic resolution.