jo1c00163_si_001.pdf (10.15 MB)
Organocatalyzed Cascade Aza-Michael/Aldol Reaction for Atroposelective Construction of 4‑Naphthylquinoline-3-carbaldehydes
journal contributionposted on 2021-02-24, 16:09 authored by Jing Zhang, Yong Xu, Zhiming Wang, Rong Zhong, Yurong Wang
An organocatalyzed cascade aza-Michael/Aldol reaction of alkynals with N-(2-(1-naphthoyl)phenyl)benzenesulfonamides has been disclosed. In the presence of a secondary amine catalyst, this method enables the construction of a series of axially chiral 4-naphthylquinoline-3-carbaldehydes in yields of up to 97% with enantioselectivities of up to 96%. Several further transformations of the synthesized products were investigated to demonstrate their synthetic applications.