title: Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles.
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.
authors.affiliation: Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
authors.forename: Vanessa
authors.initials: V
authors.lastname: Arredondo
authors.affiliation: Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
authors.forename: Stanley C
authors.initials: SC
authors.lastname: Hiew
authors.affiliation: Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
authors.forename: Eugene S
authors.initials: ES
authors.lastname: Gutman
authors.affiliation: Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
authors.forename: Ilandari Dewage Udara Anulal
authors.initials: ID
authors.lastname: Premachandra
authors.affiliation: Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
authors.forename: David L
authors.identifier: 0000-0001-5964-7042
authors.initials: DL
authors.lastname: Van Vranken
keywords: diazo compounds; heterocycles; insertion; nitrogen heterocycles; palladium