Dual C-H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels-Alder reaction

Guo-Qiang Xu; Chen-Guang Li; Ming-Qian Liu; Jian Cao; Yong-Chun Luo; Peng-Fei Xu

doi:10.1039/c5cc08833j

Dual C-H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels-Alder reaction

Chem Commun (Camb). 2016 Jan 21;52(6):1190-3. doi: 10.1039/c5cc08833j.

Authors

Guo-Qiang Xu¹, Chen-Guang Li¹, Ming-Qian Liu¹, Jian Cao¹, Yong-Chun Luo¹, Peng-Fei Xu¹

Affiliation

¹ State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China. xupf@lzu.edu.cn.

PMID: 26603196
DOI: 10.1039/c5cc08833j

Abstract

Described herein is the first example of the application of an iminium intermediate generated by visible-light photocatalyzed oxidation in an inverse electron-demand aza-Diels-Alder reaction. This dual functionalization of both C(sp(3))-H and C(sp(2))-H bonds of N-aryl tetrahydroisoquinolines represents a valuable example for access to polycycles with high diastereoselectivity.

Publication types

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