Department of Chemistry, Indian Institute of Technology , Kanpur 208016, India.
J Org Chem. 2016 Aug 5;81(15):6424-32. doi: 10.1021/acs.joc.6b01049. Epub 2016 Jul 25.
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.
已经开发出一种通过 SN2 型反应将手性纯 N-活化氮丙啶与 2-溴吲哚开环，然后进行铜催化的 C-N 环化反应来制备非外消旋四氢吡咯并[2,3-b]吲哚的新合成途径。研究了一系列具有不同取代模式的 N-活化氮丙啶和 2-溴吲哚衍生物，以高产率和优异的对映选择性（高达 99%）得到相应的四氢吡咯并[2,3-b]吲哚。从手性纯反式二取代氮丙啶中合成了高取代的四氢吡咯并[2,3-b]吲哚，其为单一立体异构体（de，ee>99%）。
