title: A Synthetic Route to Chiral Tetrahydropyrroloindoles via Ring Opening of Activated Aziridines with 2-Bromoindoles Followed by Copper-Catalyzed C-N Cyclization.
abstract: 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.
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Masthanvali
authors.initials: M
authors.lastname: Sayyad
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Mal
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Imtiyaz Ahmad
authors.initials: IA
authors.lastname: Wani
authors.affiliation: Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
authors.forename: Manas K
authors.initials: MK
authors.lastname: Ghorai