Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated N-acylpyrazoles

Pan Li; Xinquan Hu; Xiu-Qin Dong; Xumu Zhang

doi:10.1039/c6cc04987g

Rhodium/bisphosphine-thiourea-catalyzed enantioselective hydrogenation of α,β-unsaturated N-acylpyrazoles

Chem Commun (Camb). 2016 Sep 22;52(78):11677-11680. doi: 10.1039/c6cc04987g.

Authors

Pan Li¹, Xinquan Hu², Xiu-Qin Dong³, Xumu Zhang⁴

Affiliations

¹ College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. China. xumu@whu.edu.cn xiuqindong@whu.edu.cn and College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, P. R. China. xinquan@zjut.edu.cn.
² College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, P. R. China. xinquan@zjut.edu.cn.
³ College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. China. xumu@whu.edu.cn xiuqindong@whu.edu.cn.
⁴ College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. China. xumu@whu.edu.cn xiuqindong@whu.edu.cn and Department of Chemistry, South University of Science and Technology of China, Shenzhen, 518000, P. R. China.

PMID: 27709153
DOI: 10.1039/c6cc04987g

Abstract

We successfully extended our Rh/bisphosphine-thiourea (ZhaoPhos) catalytic system to asymmetric hydrogenation of α,β-unsaturated N-acylpyrazoles affording products with high yields and excellent enantioselectivities (up to 97% yield, 99% ee). The pyrazole moiety played an important role in providing H-bond acceptor sites, which is critical for achieving high reactivities and enantioselectivities.