Issue 10, 2023

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

Abstract

Enantioselective hydrogenation of α-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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Mar 2023
Accepted
09 Apr 2023
First published
10 Apr 2023

Org. Chem. Front., 2023,10, 2498-2504

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

C. Xie, Q. Guo, Z. Yang, G. Zi, Y. Huang and G. Hou, Org. Chem. Front., 2023, 10, 2498 DOI: 10.1039/D3QO00319A

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