Catalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N-Sulfonylaziridines.
Catalytic Asymmetric [3 + 2] Annulation of Hantzsch Esters with Racemic N-Sulfonylaziridines.
复制标题
DOI：
10.1021/acs.orglett.1c02931
复制
发表时间：
2021-10
期刊：
影响因子：
5.2
通讯作者：
Guo-Sheng Zhu;Pei-Jun Yang;Chen-Xue Ma;Gaosheng Yang;Zhuo Chai
中科院分区：
文献类型：
--
作者：
Guo-Sheng Zhu;Pei-Jun Yang;Chen-Xue Ma;Gaosheng Yang;Zhuo Chai
Hantzsch酯(HES)在铜(I)催化的与2-(杂芳基)-N-磺酰基氮杂环丙烷的对映体选择性[3+2]环合反应中以双碳配位，通过动力学拆分得到含有多个邻接立体中心的吡咯并[2，3-b]四氢吡啶，包括全碳季铵中心，具有良好的产率和对映体选择性以及中等到良好的非对映选择性。主要取决于氮杂环丙烷的结构，在某些情况下还观察到了以HES为氢源的竞争氢解过程。
Hantzsch esters (HEs) served as two-carbon partners in a copper(I)-catalyzed enantioselective [3 + 2] annulation with racemic 2-(hetero)aryl-N-sulfonyl aziridines via kinetic resolution to provide pyrrolo[2,3-b]tetrahydropyridines containing multiple contiguous stereogenic centers including all-carbon quaternary centers in excellent yields and enantiopurities and moderate-to-excellent diastereoselectivities. Mainly dependent upon the structures of the aziridines, a competitive hydrogenolysis process with HEs as the hydrogen source was also observed in some cases.