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- Title
Enantioselective Palladium-Catalyzed Carbene Insertion into the N−H Bonds of Aromatic Heterocycles.
- Authors
Arredondo, Vanessa; Hiew, Stanley C.; Gutman, Eugene S.; Premachandra, Ilandari Dewage Udara Anulal; Van Vranken, David L.
- Abstract
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.
- Subjects
CARBENE derivatives; PALLADIUM; HETEROCYCLIC compounds; LIGAND analysis; HYDROGEN bonding
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 15, p4220
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201611845