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

页码：3155 / 3158

页数：4

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