Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
Org Lett. 2019 Aug 2;21(15):6096-6101. doi: 10.1021/acs.orglett.9b02242. Epub 2019 Jul 24.
A highly enantioselective ring-opening desymmetrization of -aziridines with isocyanides was achieved in the presence of a chiral -dioxide/Mg(OTf) complex. The in situ generated chiral 1,4-zwitterionic intermediates were successfully trapped by intramolecular oxygen- and carbon-based nucleophiles or exogenous HO and TMSN, enabling a collective synthesis of various chiral vicinal amino-oxazoles, spiroindolines, β-amino amides, and tetrazole derivative in moderate to high yields with excellent enantioselectivities.
在手性双氧化合物/Mg(OTf)2 配合物的存在下，-氮丙啶与异氰的高对映选择性开环去对称化反应得以实现。原位生成的手性 1,4-内盐中间体可被分子内的氧和碳亲核试剂或外加的 HO 和 TMSN 成功捕获，从而实现了各种手性邻氨基恶唑、螺吲哚啉、β-氨基酸酰胺和四唑衍生物的集体合成，收率中等至高产，对映选择性优异。
