Asymmetric hydrogenation of α,β-unsaturated sulfones by a rhodium/thiourea-bisphosphine complex

被引：22

作者：

Sun, Yongjie ^{[1
]}

Jiang, Jun ^{[2
]}

Guo, Xiaochong ^{[1
]}

Wen, Jialin ^{[1
,3
]}

Zhang, Xumu ^{[1
,4
]}

机构：

[1] Southern Univ Sci & Technol, Dept Chem, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

[2] Hubei Univ, Hubei Collaborat Innovat Ctr Adv Organ Chem Mat, Wuhan, Hubei, Peoples R China

[3] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

[4] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 09期

关键词：

CYCLIC SULFONES; CHIRAL SULFONES; REDUCTION; LIGANDS; POTENT;

D O I：

10.1039/c8qo01291a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We herein report a method to synthesize chiral sulfone compounds. Catalyzed by a rhodium/ thioureabisphosphine complex, various alpha,beta-unsaturated sulfones were hydrogenated with high enantioselectivities. Kinetic studies suggested a first-order dependence of the reaction rate on the substrate concentration. Noticeable deactivation of the catalyst was observed in dichloromethane, which could be responsible for the eroded turnover number. The thiourea moiety was demonstrated to be important for high enantioselectivity and reactivity by control experiments.

引用

页码：1438 / 1441

页数：4

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