Catalytic Asymmetric Synthesis of alpha-Tetrasubstituted alpha-Trifluoromethyl Homoallylic Amines by Ir-Catalyzed Umpolung Allylation of Imines
Catalytic Asymmetric Synthesis of alpha-Tetrasubstituted alpha-Trifluoromethyl Homoallylic Amines by Ir-Catalyzed Umpolung Allylation of Imines
复制标题
Ir 催化亚胺 Umpolung 烯丙基化催化不对称合成 α-四取代 α-三氟甲基高烯丙基胺
DOI：
10.1021/acs.orglett.9b02550
复制
发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Niu Dawen
中科院分区：
文献类型：
--
作者：
Wang Yingwei;Deng Li-Fan;Zhang Xia;Niu Dawen
建立了一种制备对映体富集型α-三氟甲基、α-立体生成高烯丙基胺的通用温和方法。该反应包括Ir催化的亚胺的Um-polung烯丙基化反应和2-aza-Cope重排级联反应，可以同时产生四取代和三取代立体中心。这种转化使用了容易获得的起始材料，并显示了广阔的底物范围。反应中间体的分离和结构测定揭示了影响该转化效率和立体选择性的关键因素。
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.