Enantioselective Construction of Inherently Chiral Saddle-Shaped Azepines via Palladium-Catalyzed Intramolecular C-H Arylation.

Authors

Hao-Jie Gao, Mengfan Suo, Liping Wu, Xu Chen, Qing Liu, Haiyan Yin, Mengyao Li, Bin Yu, Wei-Tai Fan, Chuanjun Song

Published in

Organic letters. Jul 10, 2026. Epub Jul 10, 2026.

Abstract

Saddle-shaped seven-membered rings with inherent chirality remain challenging targets due to their high conformational mobility and low inversion barriers. Herein, we report a palladium-catalyzed enantioselective intramolecular C-H arylation of azepine precursors enabled by 2,2,3,3-tetramethylcyclopropylcarboxylic acid (TMCPA) as a sterically hindered carboxylic acid additive. This protocol provides efficient access to a range of inherently chiral saddle-shaped azepines in up to 96% yield and 95% ee. Thermal racemization studies further show that representative products possess useful configurational stability. We further demonstrate the synthetic applicability of this protocol and report an initial chiroptical evaluation, highlighting its potential for functional material development.

PMID:
42429462
Bibliographic data and abstract were imported from PubMed on 10 Jul 2026.

Read full publication at:
Please sign in to see all details.

Stats

1-terrible, 9-excellent. How would you rate this publication? Sign in in to submit your rating.

Post a comment

You need to be signed in to post comments. You can sign in here.

Comments

There are no comments yet.