文献类型：期刊文献

英文题名：Diastereoselective Access to Triazolo[1,2-a]indolines via a Bio- Inspired Oxidative Cyclization of NH-Indoles

作者：Yu, Lemao[1];Huang, Senhao[1];Cai, Tao[2];Du, Kui[1];Wu, Chunlei[1];Dong, Huaping[1];Shen, Runpu[2]

机构：[1]Shaoxing Univ, Sch Chem & Chem Engn, Shaoxing 312000, Peoples R China;[2]Zhejiang Engn Res Ctr FatSoluble Vitamin, Shaoxing 312000, Peoples R China

年份：0

外文期刊名：JOURNAL OF ORGANIC CHEMISTRY

收录：SCI-EXPANDED(收录号：WOS:000866253900001)、、EI(收录号：20224212969118)、Scopus(收录号：2-s2.0-85139856744)、WOS、CCR-EXPANDED(收录号：WOS:000866253900001)

基金：? ACKNOWLEDGMENTS We appreciate financial support from the National Natural Science Foundation of China (no. 21677101) and the Doctoral Research Initiation Fund of Shaoxing University. We thank Dr Cai for his help and support in crystal analysis.

语种：英文

外文摘要：Establishing three-dimensional chemicals by using the C2-C3 Z bond of indoles has always been a research hotspot in organic synthesis; however, employing the oxidative C2-C3 Z bond of indoles to generate imine which would lead to the N1-C2 Z bond cyclization under metal-free conditions is still rare. Here, we report a bio-inspired synthesis of triazolo[1,2-a]indolines by the oxidative cyclization between NH-indoles and azomethine imines with 3,3-dimethyldioxirane as the sole oxidant under metal-free and mild conditions. This finding represents an elegant instance of tri-functionalization of NH-indoles, which provides rapid access to a broad range of triazolo[1,2-a]indolines with tetrahydroisoquinolines in one single step. Up to 86% yield and above 20:1 dr value are observed. The radical mechanism and proton migration process have been speculated.