Yadav Nagendra Nath, Lee Young-Gun, Srivastava Nikhil, Ha Hyun-Joon
Department of Chemistry, North Eastern Regional Institute of Science and Technology, Nirjuli, India.
Department of Chemistry, Hankuk University of Foreign Studies, Yongin, South Korea.
Front Chem. 2019 Jun 27;7:460. doi: 10.3389/fchem.2019.00460. eCollection 2019.
Alkylative ring-opening of bicyclic aziridinium ion generated from 4-hydroxybutylaziridine with organocopper reagent was achieved successfully to afford 2-alkylsubstituted piperidine in high or moderate yield. This method allowed carbon-carbon bond formation of "non-activated" aziridine via aziridinium ion ring-opening in regio- and stereo-selective manner for the first time. This newly developed reaction was applied for an efficient synthesis of alkaloid with the representative example of conine and epiquinamide.
由4-羟基丁基氮丙啶生成的双环氮丙啶鎓离子与有机铜试剂发生烷基化开环反应，成功实现了以高或中等产率得到2-烷基取代哌啶。该方法首次通过氮丙啶鎓离子开环以区域和立体选择性的方式实现了“未活化”氮丙啶的碳-碳键形成。这种新开发的反应被应用于生物碱的高效合成，以毒芹碱和表喹酰胺为代表实例。
