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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/3063
Title: Controlling Regioselectivity in the Enantioselective N-Alkylation of Indole Analogues Catalyzed by Dinuclear Zinc-ProPhenol
Authors: Trost B.M.
Gnanamani, Elumalai
Hung C.-I.J.
Published in: Angewandte Chemie - International Edition
Abstract: The enantioselective N-alkylation of indole and its derivatives with aldimines is efficiently catalyzed by a zinc-ProPhenol dinuclear complex under mild conditions to afford N-alkylated indole derivatives in good yield (up to 86 %) and excellent enantiomeric ratio (up to 99.5:0.5 e.r.). This method tolerates a wide array of indoles, as well as pyrrole and carbazole, to afford the corresponding N-alkylation products. The reaction can be run on a gram scale with reduced catalyst loading without impacting the efficiency. The chiral aminals were further elaborated into various chiral polyheterocyclic derivatives. The surprising stability of the chiral N-alkylation products will open new windows for asymmetric catalysis and medicinal chemistry. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Citation: Angewandte Chemie - International Edition (2017), 56(35): 10451-10456
URI: https://doi.org/10.1002/anie.201705315
http://repository.iitr.ac.in/handle/123456789/3063
Issue Date: 2017
Publisher: Wiley-VCH Verlag
Keywords: asymmetric catalysis
chiral isoindolines
indoles
N-alkylation
zinc
ISSN: 14337851
Author Scopus IDs: 57217139833
35319775800
56768679500
Author Affiliations: Trost, B.M., Department of Chemistry, Stanford University, Stanford, CA 94305-5080, United States
Gnanamani, E., Department of Chemistry, Stanford University, Stanford, CA 94305-5080, United States
Hung, C.-I.J., Department of Chemistry, Stanford University, Stanford, CA 94305-5080, United States
Funding Details: We thank the National Science Foundation (CHE-1360634) and the National Institute of Health (GM-033049) for their generous support of our programs. We thank Dr. Jana Maclaren (Stanford University) for X-ray crystallographic analysis and Christopher A. Kalnmals and Jacob S. Tracy (Stanford University) for NMR experiments. E.G. is grateful for a Fulbright Nehru post-doctoral fellowship, USIEF, India.
Corresponding Author: Trost, B.M.; Department of Chemistry, Stanford UniversityUnited States; email: bmtrost@stanford.edu
Appears in Collections:Journal Publications [CY]

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