Diastereoselective synthesis of tetrahydrobenzo[<i>b</i>]azocines by Lu(OTf)<sub>3</sub>-catalyzed [4+4] cycloaddition of donor–acceptor cyclobutanes with anthranils
Meifeng Hou, Jiajun Li, Fucai Rao, Zuliang Chen, Yingjing Wei
Abstract
-catalyzed formal [4+4] cycloaddition reaction of cyclobutane 1,1-diesters with anthranils to deliver oxa-bridged eight-membered heterocycles. This methodology provides great potential to build complex azocine compounds from simple building blocks. Based on our preliminary mechanism studies, a probable mechanism for this annulation pathway has been proposed.
Topics & Concepts
CyclobutanesCyclobutaneCycloadditionChemistryAnnulationCatalysisCombinatorial chemistryStereochemistryMechanism (biology)Computational chemistryOrganic chemistryRing (chemistry)PhilosophyEpistemologyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions