College of Bioengineering, Henan University of Technology, Zhengzhou, Henan 450001, P. R. China.
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.
Chem Commun (Camb). 2019 Sep 24;55(77):11527-11530. doi: 10.1039/c9cc06249a.
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.
本文报道了通过可见光驱动的光氧化还原催化，N-芳基α-氨基酸与异喹啉 N-氧化物的[3+2]环加成反应。在无过渡金属条件下，使用二氰基吡嗪衍生的发色团（DPZ）作为光氧化还原催化剂，该转化高效，并得到了一系列重要的基于二氮杂双环[3.2.1]辛烷的 N-杂环化合物。这项工作证明了 N-芳基α-氨基酸作为 1,2-缩合试剂的合成实用性，并为异喹啉的去芳构化提供了一种新策略。
