Department of Emergency, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, and School of Chemical Engineering, Sichuan University, Chengdu, 610041, China.
Org Lett. 2019 Sep 6;21(17):6951-6956. doi: 10.1021/acs.orglett.9b02550. Epub 2019 Aug 16.
A general and mild method to prepare enantioenriched α-trifluoromethyl, α-stereogenic homoallylic amines is established. This reaction, which involves an Ir-catalyzed umpolung allylation of imines and a 2-aza-Cope rearrangement cascade, could yield both tetrasubstituted and trisubstituted stereocenters. This transformation employs readily available starting materials and displays broad substrate scope. The isolation and structural determination of reaction intermediates revealed factors critical for the efficiency and stereoselectivity of this transformation.
建立了一种通用且温和的方法来制备对映体富集的α-三氟甲基、α-手性偕丙基胺。该反应涉及 Ir 催化的亚胺的反转烯丙基化和 2-氮杂-Cope 重排级联反应，可生成四取代和三取代的立体中心。该转化采用易得的起始原料，具有广泛的底物范围。反应中间体的分离和结构测定揭示了对该转化的效率和立体选择性至关重要的因素。
