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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