Thermodynamic Controlled Regioselective C1-Functionalization of Indolizines with 3-Hydroxyisoindolinones via Brønsted Acid Catalyzed aza-Friedel–Crafts Reaction
Zhiming Zhu, Qianling Wu, Xiaoxiao Song, Qijian Ni
Abstract
A Brønsted acid catalyzed aza-Friedel-Crafts reaction of indolizines with 3-hydroxyisoindolinones has been established, which constructs isoindolinone derivatives bearing a tetrasubstituted stereocenter in good to high yields and enantioselectivities. Notably, this strategy provides a new access to C1-functionalization of indolizines with excellent regioselectivities. Moreover, this intriguing C1-regioselective transformation was induced under thermodynamic control.
Topics & Concepts
RegioselectivityChemistryFriedel–Crafts reactionStereocenterBrønsted–Lowry acid–base theoryCatalysisSurface modificationOrganic chemistryOrganocatalysisCombinatorial chemistryEnantioselective synthesisPhysical chemistrySynthesis and Reactivity of HeterocyclesCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms