College of Material Science & Engineering , Taiyuan University of Technology , Shanxi 030024 , China.
Department of Chemistry, Shenzhen Grubbs Institute , Southern University of Science and Technology , Shenzhen 518055 , China.
Org Lett. 2018 Oct 5;20(19):6022-6026. doi: 10.1021/acs.orglett.8b02361. Epub 2018 Sep 17.
For the first time, a desymmetrization strategy empowered the assembly of a class of optically pure spirooxindole-urazoles possessing an N-Ar stereogenic axis via remote control of axial chirality in an asymmetric three-component reaction. This transformation was realized by a tandem bisthiourea-catalyzed asymmetric Diels-Alder reaction and substrate-controlled asymmetric ene reaction. The driving force derived from aromatization and the high reactivity of 4-aryl-1,2,4-triazole-3,5-dione enophiles mediated the occurrence of the successive ene reaction under mild conditions.
首次采用去对称化策略，通过不对称三组分反应中轴手性的远程控制，实现了一类具有 N-Ar 立体轴的光学纯螺噁吲哚-尿嘧啶的组装。这种转化是通过串联双硫脲催化的不对称 Diels-Alder 反应和底物控制的不对称烯反应来实现的。芳香化的驱动力和 4-芳基-1,2,4-三唑-3,5-二酮亲电试剂的高反应性在温和条件下促进了连续烯反应的发生。
