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

共 50 条

[1] Organocatalytic asymmetric synthesis of benzothiazolopyrimidines via a [4+2] cycloaddition of azlactones with 2-benzothiazolimines
Ke, Chaoqi
Liu, Zhenzhong
Ruan, Sai
Feng, Xiaoming
Liu, Xiaohua
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (20) : 5705 - 5709
[2] Organocatalytic Asymmetric Synthesis of Benzothiazolopyrimidines via [4+2] Cyclization of 2-Benzothiazolimines and Aldehydes
Chen, Xue-Ping
Hou, Ke-Qiang
Zhou, Feng
Chan, Albert S. C.
Xiong, Xiao-Feng
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (02): : 1667 - 1675
[3] Organocatalytic Asymmetric [4+2] Cyclization of Azadienes with Azlactones: Access to Chiral 3-Amino-d-Lactams Derivatives
Zhou, Wu-Jingyun
Yu, Xiaoning
Chen, Chen
Lan, Wei
Zhan, Gu
Zhou, Jin
Liu, Qian
Huang, Wei
Yang, Qian-Qian
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13427 - 13439
[4] Asymmetric Mannich/Cyclization Reaction of 2-Benzothiazolimines and 2-Isothiocyano-1-indanones to Construct Chiral Spirocyclic Compounds
Zheng, Yao
Du, Da-Ming
MOLECULES, 2024, 29 (13):
[5] Asymmetric Synthesis of 3,4-Dihydroquinolin-2-ones via Organocatalytic [4+2]-Cyclization of 2-Amino-β-nitrostyrenes with Azlactones
Kim, Heebum
Kim, Yeongju
Kim, Sung-Gon
ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (08) : 1756 - 1762
[6] Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4+2] cyclization reaction of dioxopyrrolidines and azlactones
Wang, Yichen
Chen, Yuzhen
Li, Xiaoping
Mao, Yukang
Chen, Weiwen
Zhan, Ruoting
Huang, Huicai
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (16) : 3945 - 3950
[7] Organocatalytic Asymmetric [4+2] Cycloaddition Reactions
Wang Chun
Liu Weihua
Zhou Xin
Li Yuemin
Li Yunpeng
PROGRESS IN CHEMISTRY, 2009, 21 (09) : 1857 - 1868
[8] Asymmetric [4+2] cycloaddition of azlactones with dipolar copper-allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives
Sun, Bing-Bing
Hu, Qing-Xian
Hu, Jia-Ming
Yu, Jie-Qiang
Jia, Jun
Wang, Xing-Wang
TETRAHEDRON LETTERS, 2019, 60 (30) : 1967 - 1970
[9] Diastereo- and Enantioselective Mannich/Cyclization Cascade Reaction Access to Chiral Benzothiazolopyrimidine Derivatives
Zhang, Yan
Yang, Jia-Hui
Xia, Ying-Qi
Dong, Lin
Chen, Fen-Er
CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (20) : 6183 - 6186
[10] Access to Metal-Bridged Osmathiazine Derivatives by a Formal [4+2] Cyclization
Li, Jinhua
Lin, Yu-Mei
Zhang, Hong
Chen, Yuan
Lin, Zhenyang
Xia, Haiping
CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (19) : 5077 - 5085

← 1 2 3 4 5 →