Wani, Imtiyaz Ahmad ; Das, Subhomoy ; Mondal, Shobhan ; Ghorai, Manas K. (2018) Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3-Methylindoles and Carbonyls The Journal of Organic Chemistry, 83 (23). pp. 14553-14567. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.8b02339
Related URL: http://dx.doi.org/10.1021/acs.joc.8b02339
Abstract
A highly efficient and stereoselective route to access 1,3-disubstituted 1,2,3,4-tetrahydropyrazino[1,2-a]indoles and 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indoles with excellent stereoselectivity (de, ee >99%) via base mediated ring opening of aziridines/epoxides with 3-methylindoles followed by BF3·OEt2 catalyzed Pictet-Spengler reaction is accomplished. Interestingly, PTSA promoted cyclization led to the formation of oxidized 3,4-dihydropyrazino[1,2-a]indoles in excellent yields via an unprecedented Pictet-Spengler-detosylation cascade.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 117083 |
| Deposited On: | 15 Apr 2021 07:42 |
| Last Modified: | 15 Apr 2021 07:42 |
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