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A Bulky Chiral N‐Heterocyclic Carbene Nickel Catalyst Enables Enantioselective C−H Functionalizations of Indoles and Pyrroles
Author(s) -
Diesel Johannes,
Grosheva Daria,
Kodama Shota,
Cramer Nicolai
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904774
Subject(s) - carbene , enantioselective synthesis , chemistry , catalysis , nickel , combinatorial chemistry , yield (engineering) , ligand (biochemistry) , ring (chemistry) , stereochemistry , organic chemistry , materials science , receptor , biochemistry , metallurgy
An enantioselective nickel(0)‐catalyzed C−H functionalization of indoles and pyrroles that does not require the typical Lewis basic directing groups is disclosed. The reaction provides access to valuable tetrahydropyridoindoles and tetrahydroindolizines in high yields and enantioselectivity under mild reaction conditions. The process is characterized by a clear endo ‐cyclization preference to yield the sought‐after six‐membered‐ring products. Key for the success of the activation and selectivity in the cyclization was the development of a novel chiral SIPr carbene ligand analogue with very bulky flanking groups.