Zhang Fengcai, Zhang Yu, Tan Qingfa, Lin Lili, Liu Xiaohua, Feng Xiaoming
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.
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。
