Rhodium‐Catalyzed Dynamic Kinetic [4+2] Cycloaddition of Allene‐1,3‐Dienes
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Abstract
Rh-catalyzed dynamic kinetic intramolecular [4+2] cycloaddition reaction of 1,3-disubstituted allene-1,3-dienes afforded cis-fused [4.3.0]bicyclic products with an excellent chemo-, diastereo-, and enantio-selectivity. Many synthetically useful functional groups are tolerated. The synthetic utility has been demonstrated. Based on the careful experimental studies, a mechanism involving the rapid racemization of the allene moiety in the starting materials has been proposed.
Topics & Concepts
AlleneCycloadditionRhodiumMoietyChemistryRacemizationIntramolecular forceBicyclic moleculeCatalysisSelectivityCombinatorial chemistryStereochemistryOrganic chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms