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Stereoselective Construction of Pyrazinoindoles and Oxazinoindoles via Ring-Opening/Pictet-Spengler Reaction of Aziridines and Epoxides with 3‑Methylindoles and Carbonyls

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journal contribution
posted on 08.11.2018, 00:00 by Imtiyaz Ahmad Wani, Subhomoy Das, Shobhan Mondal, Manas K. Ghorai
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.