National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, China.
Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu 610106, China.
Org Biomol Chem. 2023 Feb 15;21(7):1373-1378. doi: 10.1039/d2ob02303b.
A formal [4 + 2] cycloaddition of 3-nitroindoles with -aminophenyl -quinone methides a dearomatization process was developed. This method provides a facile approach for preparing tetrahydro-5-indolo[2,3-]quinolones with good results. With the bifunctional alkaloid-squaramide as the catalyst, the asymmetric version of the reaction successfully afforded the corresponding chiral products with moderate to good enantioselectivities. This work represents the first dearomative cycloaddition of electron-deficient heteroarenes triggered by aza-Michael addition from -QMs.
开发了一种 3-硝基吲哚与-氨苯基-醌甲亚胺的[4+2]环加成的去芳构化过程。该方法为制备四氢-5-吲哚[2,3-]喹啉酮提供了一种简便的方法，产率良好。使用双功能生物碱-螺二酰胺作为催化剂，该反应的不对称版本成功地得到了具有中等至良好对映选择性的相应手性产物。这项工作代表了由 aza-Michael 加成引发的缺电子杂芳烃的首次去芳构化环加成。
