Ruthenium-Catalyzed Ring-Opening Addition of Anilides to 7-Azabenzonorbornadienes: A Diastereoselective Route to Hydronaphthylamines

Qiangqiang Yan; Chunhua Xiong; Steven Chu; Zhanxiang Liu; Yuhong Zhang

doi:10.1021/acs.joc.8b00604

Ruthenium-Catalyzed Ring-Opening Addition of Anilides to 7-Azabenzonorbornadienes: A Diastereoselective Route to Hydronaphthylamines

J Org Chem. 2018 May 18;83(10):5598-5608. doi: 10.1021/acs.joc.8b00604. Epub 2018 Apr 27.

Authors

Qiangqiang Yan¹, Chunhua Xiong², Steven Chu¹, Zhanxiang Liu¹, Yuhong Zhang^{1

3}

Affiliations

¹ Department of Chemistry , Zhejiang University , Hangzhou 310027 , China.
² Department of Applied Chemistry , Zhejiang Gongshang University , Hangzhou 310012 , China.
³ State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , China.

PMID: 29667826
DOI: 10.1021/acs.joc.8b00604

Abstract

The ruthenium(II)-catalyzed direct ring-opening reaction of 7-azabenzonorbornadienes with anilides via C-H activation to access hydronaphthylamines has been developed. The transformation proceeds with a high stereoselectivity to give cis-configuration products under redox-neutral conditions.

Publication types

Research Support, Non-U.S. Gov't