Chiral Phosphoric Acid-Catalyzed Asymmetric Friedel–Crafts Addition of Indolizine to Cyclic <i>N</i>-Sulfonyl Imine
Parbat Subba, Milon M. Sadhu, Vinod K. Singh
Abstract
A highly efficient chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts addition of indolizine to cyclic N -sulfonyl imine has been established. The newly developed protocol, which probably proceeds via a monoactivation reaction pathway, allows the access of enantioenriched sulfonamide functionalized indolizines with excellent yields (up to 99%) and enantioselectivities (up to 99%). Moreover, the synthetic utility of this protocol has been explored with some chemical transformations.
Topics & Concepts
Enantioselective synthesisChemistryIndolizineImineSulfonamidePhosphoric acidFriedel–Crafts reactionSulfonylCatalysisOrganic chemistryCombinatorial chemistryAlkylSynthesis and Reactivity of HeterocyclesCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods