Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 16, Pages 9086-9092Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202017268
Keywords
Brø nsted acid catalysis; desymmetrization; dynamic kinetic resolution; indole; phosphoric acid
Categories
Funding
- Science and Engineering Research Board (SERB), New Delhi [EMR/2016/005045]
- IISc Bangalore
- Department of Science and Technology (DST)-FIST grant [SR/FST/CS II-040/2015]
Ask authors/readers for more resources
The first catalytic enantioselective Fischer indolization of prochiral diketones containing enantiotopic carbonyl groups is developed through dynamic kinetic resolution. Catalyzed by a combination of a spirocyclic chiral phosphoric acid and ZnCl2, this approach efficiently synthesizes cyclopenta[b]indole derivatives with an all-carbon quaternary stereocenter in good to excellent enantioselectivities.
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 Bronsted 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available