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Enantioselective Palladium‐Catalyzed Carbene Insertion into the N−H Bonds of Aromatic Heterocycles
Author(s) -
Arredondo Vanessa,
Hiew Stanley C.,
Gutman Eugene S.,
Premachandra Ilandari Dewage Udara Anulal,
Van Vranken David L.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201611845
Subject(s) - carbene , palladium , chemistry , enantioselective synthesis , carbazole , ligand (biochemistry) , oxazoline , catalysis , aryl , combinatorial chemistry , medicinal chemistry , organic chemistry , alkyl , receptor , biochemistry
C3‐substituted indoles and carbazoles react with α‐aryl‐α‐diazoesters under palladium catalysis to form α‐(N‐indolyl)‐α‐arylesters and α‐(N‐carbazolyl)‐α‐arylesters. The products result from insertion of a palladium‐carbene ligand into the N−H bond of the aromatic N‐heterocycles. Enantioselection was achieved using a chiral bis(oxazoline) ligand, in many cases with high enantioselectivity (up to 99 % ee). The method was applied to synthesize the core of a bioactive carbazole derivative in a concise manner.