Organocatalyzed Cascade Aza-Michael/Aldol Reaction for Atroposelective Construction of 4-Naphthylquinoline-3carbaldehydes

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.

Automated summary

An organocatalyzed cascade reaction was developed for the construction of axially chiral compounds with high yields and enantioselectivities. Further transformations of the synthesized products were explored to illustrate their synthetic applications.