Catalytic Enantioselective Desymmetrizing Fischer Indolization through Dynamic Kinetic Resolution
Biki Ghosh, Reena Balhara, Garima Jindal, Santanu Mukherjee
Abstract
Abstract The first catalytic enantioselective Fischer indolization of prochiral diketones containing enantiotopic carbonyl groups is developed and shown to proceed through dynamic kinetic resolution (DKR). Catalyzed by the combination of a spirocyclic chiral phosphoric acid and ZnCl 2 (Lewis acid assisted Brønsted acid), this direct approach combines 2,2‐disubstituted cyclopentane‐1,3‐diones with N ‐protected phenylhydrazines to furnish cyclopenta[ b ]indole derivatives containing an all‐carbon quaternary stereocenter with good to excellent enantioselectivities.
Topics & Concepts
StereocenterKinetic resolutionEnantioselective synthesisCyclopentaneChemistryCatalysisPhosphoric acidBrønsted–Lowry acid–base theoryOrganic chemistryIndole testLewis acids and basesStereochemistryAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and CatalysisMolecular spectroscopy and chirality