Asymmetric hydrogenation of alpha,beta-unsaturated sulfones by a rhodium/thiourea-bisphosphine complex

Sun, Yongjie1; Jiang, Jun2; Guo, Xiaochong1; Wen, Jialin1,3; Zhang, Xumu1,4

2019-05-07

10.1039/c8qo01291a

Organic Chemistry Frontiers   影响因子和分区

2052-4129

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.

SCI ; EI ; IC ; CCR

英语

第一 ; 通讯

Natural Science Foundation of Hubei Province[2018CFB307]

Chemistry

Chemistry, Organic

WOS:000466794900016

ROYAL SOC CHEMISTRY

20191806864074

Dichloromethane ; Enantioselectivity ; Hydrogenation

Physical Chemistry:801.4 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

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

Sun, Yongjie,Jiang, Jun,Guo, Xiaochong,et al. Asymmetric hydrogenation of alpha,beta-unsaturated sulfones by a rhodium/thiourea-bisphosphine complex[J]. Organic Chemistry Frontiers,2019,6(9):1438-1441.

Sun, Yongjie,Jiang, Jun,Guo, Xiaochong,Wen, Jialin,&Zhang, Xumu.(2019).Asymmetric hydrogenation of alpha,beta-unsaturated sulfones by a rhodium/thiourea-bisphosphine complex.Organic Chemistry Frontiers,6(9),1438-1441.

Sun, Yongjie,et al."Asymmetric hydrogenation of alpha,beta-unsaturated sulfones by a rhodium/thiourea-bisphosphine complex".Organic Chemistry Frontiers 6.9(2019):1438-1441.