Stereoselective construction of 5-6-5 aza-tricyclic scaffolds via catalytic asymmetric aza-Piancatelli/Diels–Alder reactions

Abstract

A chiral Brønsted acid-catalyzed asymmetric cascade aza-Piancatelli rearrangement/intramolecular Diels–Alder reaction has been developed. This method enables the atom- and step-efficient synthesis of chiral aza-[5,6,5]-tricyclic derivatives with multiple contiguous stereocenters in a highly enantioselective manner from readily available N-pentadienylanilines and 2-furylcarbinols.