Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides

Xiangyuan Liu; Yanli Yin; Zhiyong Jiang

doi:10.1039/c9cc06249a

Photoredox-catalysed formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides

Chem Commun (Camb). 2019 Sep 24;55(77):11527-11530. doi: 10.1039/c9cc06249a.

Authors

Xiangyuan Liu¹, Yanli Yin², Zhiyong Jiang³

Affiliations

¹ College of Bioengineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China. yinzihust@163.com and Henan University, Kaifeng, Henan 475004, P. R. China.
² College of Bioengineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China. yinzihust@163.com.
³ Henan University, Kaifeng, Henan 475004, P. R. China and Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China. jiangzhiyong@htu.edu.cn chmjzy@henu.edu.cn.

PMID: 31490488
DOI: 10.1039/c9cc06249a

Abstract

A formal [3+2] cycloaddition of N-aryl α-amino acids with isoquinoline N-oxides via visible light-driven photoredox catalysis is reported. Under transition metal-free conditions using a dicyanopyrazine-derived chromophore (DPZ) as the photoredox catalyst, the transformation was efficient and led to a series of important diazabicyclo[3.2.1]octane-based N-heterocyclic compounds. This work demonstrates the synthetic utility of N-aryl α-amino acids as 1,2-synthons and provides a new strategy for the dearomatization of isoquinolines.