Organocatalytic asymmetric synthesis of axially and centrally chiral heterotriarylmethanes by a Friedel–Crafts reaction

Abstract

A highly enantioselective Friedel–Crafts reaction between C2-unsubstituted naphthyl-indoles and racemic 3-methylated-3H-pyrrolides catalyzed by chiral phosphoric acids has been developed. This reaction provides an efficient and facile route to a series of heterotricyclic triarylmethanes containing axially chiral naphthyl-indole and centrally chiral pyrrole moieties under mild conditions. Moreover, biological evaluation discovered one of these products with promising antitumor activity, and demonstrates its potential application in medicinal chemistry.