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Catalytic Enantioselective Desymmetrizing Fischer Indolization through Dynamic Kinetic Resolution
Author(s) -
Ghosh Biki,
Balhara Reena,
Jindal Garima,
Mukherjee Santanu
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202017268
Subject(s) - stereocenter , enantioselective synthesis , kinetic resolution , cyclopentane , chemistry , catalysis , brønsted–lowry acid–base theory , phosphoric acid , organic chemistry , organocatalysis , lewis acids and bases , indole test , stereochemistry , combinatorial chemistry
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.