Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Brønsted acid catalysis

Abstract

An efficient relay catalytic process involving Au(I)/Brønsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel–Crafts-type reaction generating functionalized cyclopenta[b]indoles.