Stereoselective construction of novel biaryl bridged seven-membered ring scaffolds via intramolecular [3 + 2] cycloaddition reactions

Abstract

A novel approach to biaryl bridged seven-membered carbocyclic scaffolds was developed by means of an intramolecular [3 + 2] cycloaddition process of in situ formed azomethine ylides from 2-cinnamoyl-2'-formyl biphenyl and diethyl aminomalonate hydrochloride. A range of biaryl bridged carbocyclic motifs with five-membered pyrrole ring bearing three steregenic centers was achieved with good to excellent yields (up to 98%) along with excellent diastereoselectivities (up to >20:1 dr).