Catalytic Enantioselective Desymmetrizing Fischer Indolization through Dynamic Kinetic Resolution
Biki Ghosh
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorReena Balhara
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Garima Jindal
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Santanu Mukherjee
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorBiki Ghosh
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorReena Balhara
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Garima Jindal
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorCorresponding Author
Prof. Dr. Santanu Mukherjee
Department of Organic Chemistry, Indian Institute of Science, Bangalore, 560 012 India
Search for more papers by this authorGraphical Abstract
The first catalytic enantioselective desymmetrizing Fischer indolization of prochiral diketones, containing enantiotopic carbonyl groups, is developed and shown to proceed through dynamic kinetic resolution. Catalyzed by a combination of a spirocyclic chiral phosphoric acid and ZnCl2, this reaction delivers cyclopenta[b]indolones, containing an all-carbon quaternary stereocenter, with up to 98.5:1.5 e.r.
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.
Conflict of interest
The authors declare no conflict of interest.
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