Catalyst-Controlled Divergent Intramolecular Cyclizations of Morita–Baylis–Hillman Carbonates
Wei Cai, Yanlin He, Yiming Zhou, You Huang
Abstract
Unprecedented catalyst-controlled divergent cyclizations of Morita–Baylis–Hillman carbonates have been established using either Cs2CO3 or quinuclidine as the catalyst. 1,2-Dihydroquinolines and 4H-3,1-benzoxazines were efficiently synthesized via SN2′ and SN2′–SN2′ processes, respectively. DFT calculations have led to a deeper understanding of these reaction modes and chemoselectivity.
Topics & Concepts
SN2 reactionChemoselectivityCatalysisIntramolecular forceQuinuclidineChemistryComputational chemistryOrganic chemistryStereochemistrySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsCatalytic C–H Functionalization Methods