One-Pot Enantioselective Construction of Polycyclic Tetrahydroquinoline Scaffolds through Asymmetric Organo/Photoredox Catalysis via Triple-Reaction Sequence

Jia-Lu Zhang, Jin-Yu Liu, Guo-Qiang Xu, Yong-Chun Luo, Hong Lu, Chang-Yin Tan, Xiu-Qin Hu*, and Peng-Fei Xu*

https://doi.org/10.1021/acs.orglett.1c00712

Abstract

A novel one-pot triple-reaction strategy for the asymmetric construction of polycyclic skeletons with multiple consecutive chiral centers through aza-Michael/Michael/Wittig/ketyl radical addition/esterification processes is reported. A wide range of polycyclic tetrahydroquinoline derivatives were smoothly obtained from easily available starting materials with good results (up to 80% yield, >20:1 dr, >99% ee) under mild conditions. In this transformation, five chemical bonds and five consecutive chiral centers were successively formed.