Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031

Zhu, Tiao-Zhen1; Shao, Pan-Lin1; Zhang, Xumu2

2021-04-01

10.1039/d1qo00368b

Organic Chemistry Frontiers   影响因子和分区

2052-4129

Due to their stereoelectronic properties, trifluoromethyl (or perfluoroalkyl) ketones are challenging substrates in asymmetric (transfer) hydrogenation. We have developed iridium/f-amphol and iridium/f-ampha catalysis systems, which provide a highly efficient method for the synthesis of chiral secondary 2,2,2-trifluoroethanols in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee). The practicability of this methodology was demonstrated through the facile preparation of the key intermediates of Odanacatib and LX-1301.

SCI ; EI

英语

第一 ; 通讯

Science, Technology and Innovation Commission of Shenzhen["JCYJ20190809160211372","KQTD20150717103157174"] ; National Natural Science Foundation of China[21991113] ; Shenzhen Clean Energy Research Institute[CERI-KY-2019-003] ; Guangdong Provincial Key Laboratory of Catalysis[2020B121201002]

Chemistry

Chemistry, Organic

WOS:000647826200001

ROYAL SOC CHEMISTRY

20212910653456

Catalysis ; Iridium ; Ketones

Precious Metals:547.1 ; Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Southern Univ Sci & Technol, Coll Innovat & Entrepreneurship, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Dept Chem, Guangdong Prov Key Lab Catalysis, 1088 Xueyuan Rd, Shenzhen 518055, Peoples R China

Zhu, Tiao-Zhen,Shao, Pan-Lin,Zhang, Xumu. Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031[J]. Organic Chemistry Frontiers,2021,8:3705-3711.

Zhu, Tiao-Zhen,Shao, Pan-Lin,&Zhang, Xumu.(2021).Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031.Organic Chemistry Frontiers,8,3705-3711.

Zhu, Tiao-Zhen,et al."Asymmetric hydrogenation of trifluoromethyl ketones: application in the synthesis of Odanacatib and LX-1031".Organic Chemistry Frontiers 8(2021):3705-3711.