Organocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives

被引：29
|
作者：
Ni, Qijian [1 ]
Wang, Xuyang [1 ]
Xu, Fangfang [1 ]
Chen, Xiaoyun [2 ]
Song, Xiaoxiao [1 ]
机构：
[1] Anhui Normal Univ, Coll Chem & Mat Sci, Key Lab Functionalized Mol Solids, Minist Educ,Anhui Lab Mol Based Mat, Wuhu 241002, Anhui, Peoples R China
[2] Jiangsu Univ Sci & Technol, Sch Environm & Chem Engn, Zhenjiang 212003, Jiangsu, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2020年 / 56卷 / 21期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTIONS; MANNICH-TYPE REACTION; ONE-POT SYNTHESIS; KINETIC RESOLUTION; 1,3-DIPOLAR CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; QUINONE METHIDES; QUATERNARY; DIHYDROCOUMARINS; CONSTRUCTION;
D O I：
10.1039/d0cc00736f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An organocatalytic asymmetric domino Mannich/cyclization reaction between 2-benzothiazolimines with azlactones has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20 : 1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines bearing adjacent tertiary and quaternary stereogenic centers.
引用
收藏
页码：3155 / 3158
页数：4
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