Sayyad, Masthanvali ; Wani, Imtiyaz Ahmad ; Babu, Raja ; Nanaji, Yerramsetti ; Ghorai, Manas K. (2017) A Synthetic Route to Chiral 1,4-Disubstituted Tetrahydro-β-Carbolines via Domino Ring-Opening Cyclization of Activated Aziridines with 2-Vinylindoles The Journal of Organic Chemistry, 82 (5). pp. 2364-2374. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.6b02719
Related URL: http://dx.doi.org/10.1021/acs.joc.6b02719
Abstract
A simple and efficient strategy for the synthesis of various 1,4-disubstituted tetrahydro-β-carbolines with excellent stereoselectivity (de, ee up to >99%) via domino ring opening cyclization (DROC) of activated aziridines with 2-vinylindoles is described. The reaction proceeds through LiClO4-catalyzed Friedel–Crafts-type alkylation of 2-vinylindoles with activated aziridines followed by an intramolecular aza-Michael reaction in a domino fashion.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117095 |
| Deposited On: | 15 Apr 2021 07:45 |
| Last Modified: | 15 Apr 2021 07:45 |
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