A Synthetic Route to
Chiral Tetrahydropyrroloindoles
via Ring Opening of Activated Aziridines with 2‑Bromoindoles
Followed by Copper-Catalyzed C–N Cyclization
posted on 2016-07-11, 00:00authored byMasthanvali Sayyad, Abhijit Mal, Imtiyaz Ahmad Wani, Manas K. Ghorai
A new
synthetic route to nonracemic tetrahydropyrrolo[2,3-b]indoles has been developed via SN2-type ring
opening of enantiopure N-activated aziridines with 2-bromoindoles
followed by copper-catalyzed C–N cyclization. A series of N-activated
aziridines and 2-bromoindole derivatives with different substitution
patterns were studied to afford the corresponding tetrahydropyrrolo[2,3-b]indoles in good yields and excellent ee (up to 99%). Highly
substituted tetrahydropyrrolo[2,3-b]indole was synthesized
as a single stereoisomer (de, ee >99%) from enantiopure trans-disubstituted aziridine.