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Catalytic Enantioselective Desymmetrizing Fischer Indolization through Dynamic Kinetic Resolution
Biki Ghosh1, Reena Balhara1, Garima Jindal1
1Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012, India.
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 ZnCl2 (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.
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