通过与巯基苯并噻唑的催化不对称开环反应实现氮杂环丙烷的动力学拆分
Kinetic Resolution of Aziridines via Catalytic Asymmetric Ring-Opening Reaction with Mercaptobenzothiazoles.
作者信息
Zhang Fengcai, Zhang Yu, Tan Qingfa, Lin Lili, Liu Xiaohua, Feng Xiaoming
机构信息
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
Collaborative Innovation Center of Chemical Science and Engineering , Tianjin 300072 , China.
出版信息
Org Lett. 2019 Aug 2;21(15):5928-5932. doi: 10.1021/acs.orglett.9b02058. Epub 2019 Jul 23.
A highly efficient kinetic resolution of racemic 2-acyl-3-aryl--tosylaziridines is achieved through a chiral Lewis acid promoted ring-opening reaction with 2-mercaptobenzothiazoles as the nucleophiles. The chiral -dioxide-lanthanum complex as catalyst and the 2-mercaptobenzothiazoles as active sulfur nucleophiles are the keys to the success of the reaction. A variety of enantioenriched β-amino thioethers and aziridines are obtained in good yields with good ee values.
通过手性路易斯酸促进的开环反应，以2-巯基苯并噻唑作为亲核试剂，实现了外消旋2-酰基-3-芳基-对甲苯磺酰氮丙啶的高效动力学拆分。手性二氧化物-镧配合物作为催化剂，2-巯基苯并噻唑作为活性硫亲核试剂是该反应成功的关键。以良好的对映体过量值高产率地获得了多种对映体富集的β-氨基硫醚和氮丙啶。
Zotero 插件