Enantioselective synthesis of chiral 2,2,2-trifluoroethyl lactams via asymmetric hydrogenation

被引：6

作者：

Xie, Chaochao ^{[1
]}

Guo, Qianling ^{[1
]}

Yang, Zhihong ^{[1
]}

Zi, Guofu ^{[1
]}

Huang, Yuping ^{[2
]}

Hou, Guohua ^{[1
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Key Lab Radiopharmaceut, Beijing 100875, Peoples R China

[2] SINOPEC, Res Inst Petr Proc, Beijing 100083, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 10期

基金：

北京市自然科学基金; 中国国家自然科学基金;

关键词：

CATALYZED TRIFLUOROMETHYLATION; FLUORINE; CONSTRUCTION; ACID; ALPHA-CF3; CARBONYL; OLEFINS; ARENES;

D O I：

10.1039/d3qo00319a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantioselective hydrogenation of a-trifluoromethylidene lactams catalyzed by the Rh/f-spiroPhos complex has been first developed. The method provides an efficient and highly enantioselective approach for the synthesis of a variety of chiral 2,2,2-trifluoroethyl lactams with excellent enantioselectivities (up to 99.9% ee) and high turnover numbers (TON of up to 10 500). Moreover, the obtained hydrogenation products were also successfully transformed into chiral 2,2,2-trifluoroethyl pyrrolidine, 2-piperidone, and an inhibitor of the donor receptor tyrosine kinase effector Raf.

引用

页码：2498 / 2504

页数：7

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