A Enamide-Based Diastereoselective Synthesis of Isoindolo[2,1-a]quinolin-11(5H)-ones with Three Contiguous Stereogenic Centers

A stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones containing three contiguous stereogenic centers is described. This Lewis-acid mediated reaction of enamides with N-aryl-acylimines affords the desired fused heterocyclic isoindolinones in high yields and diastereoselectivities. Scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.

Automated summary

This article describes a stereoselective synthesis of isoindolo[2,1-a]quinolin-11(5H)-ones that contain three contiguous stereogenic centers. The desired fused heterocyclic isoindolinones are obtained in high yields and diastereoselectivities through a Lewis-acid mediated reaction of enamides with N-aryl-acylimines. The scope and limitations of this method are discussed. The stereochemical outcome of this transformation indicates a stepwise reaction pathway.