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Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles. 2017
Vanessa Arredondo, and
Stanley C Hiew, and
Eugene S Gutman, and
Ilandari Dewage Udara Anulal Premachandra, and
David L Van Vranken
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences II, Irvine, CA, 92697, USA.
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.
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