Department of Chemistry, Hankuk University of Foreign Studies, Yongin 17035, Korea.
Org Biomol Chem. 2020 Dec 7;18(46):9473-9482. doi: 10.1039/d0ob01865a.
Lewis acid-mediated regio- and stereoselective nucleophilic addition of 2- or 3-substituted indoles to non-activated aziridine-2-carboxaldehydes in dioxane afforded 2-(indol-3-ylhydroxymethyl)aziridines whose ring opening with various nucleophiles rendered multi-substituted tryptamine derivatives. The reaction of the same aziridine-2-carboxaldehyde with three moles of indole in dichloromethane yielded tris-indole adducts β-(3,3'-bisindolyl)methyl (BIM) tryptamines from sequential steps including nucleophilic addition to aldehyde, Michael type Friedel-Crafts alkylation of the mono-adduct followed by regio- and stereoselective ring-opening of the aziridine ring.
路易斯酸介导的 2-或 3-取代吲哚对非活化氮丙啶-2-甲醛的区域和立体选择性亲核加成，在二氧六环中得到 2-(吲哚-3-羟甲基)氮丙啶，其与各种亲核试剂开环得到多取代色胺衍生物。相同的氮丙啶-2-甲醛与三摩尔吲哚在二氯甲烷中的反应，通过包括醛的亲核加成、单加成物的迈克尔型傅克烷基化反应以及氮丙啶环的区域和立体选择性开环的顺序步骤，生成三吲哚加合物β-(3,3'-二吲哚基)甲基（BIM）色胺。
