Organocatalytic enantioselective Mannich-type addition of 5H-thiazol-4-ones to isatin-derived imines: access to 3-substituted 3-amino-2-oxindoles featured by vicinal sulfur-containing tetrasubstituted stereocenters

被引：32

作者：

Huang, Qiuhong ^{[1
]}

Cheng, Yuyu ^{[2
]}

Yuan, Huijun ^{[1
]}

Chang, Xiaoyong ^{[2
]}

Li, Pengfei ^{[2
]}

Li, Wenjun ^{[1
]}

机构：

[1] Qingdao Univ, Sch Pharm, Dept Med Chem, Qingdao 266021, Shandong, Peoples R China

[2] Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Guangdong, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 22期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 4+2 ANNULATION; CONSTRUCTION; KETIMINES; SCAFFOLDS; BEARING; 5H-OXAZOL-4-ONES; THIOETHERS; OXINDOLES;

D O I：

10.1039/c8qo00814k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first chiral phosphoric acid catalyzed enantioselective nucleophilic addition of 5H-thiazol-4-ones to isatin-derived imines has been established. By using this strategy, the resulting 3-substituted 3-amino-2-oxindoles featuring both 5H-thiazol-4-one and vicinal sulfur-containing tetrasubstituted stereocenter structural motifs were obtained in high yields with excellent enantioselectivities and diastereoselectivities.

引用

页码：3226 / 3230

页数：5

共 5 条

[1] Enantioselective Construction of Vicinal Sulfur-containing Tetrasubstituted Stereocenters via Organocatalyzed Mannich-Type Addition of Rhodanines to Isatin Imines
Huang, Qiuhong
Zhang, Lili
Cheng, Yuyu
Li, Pengfei
Li, Wenjun
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (17) : 3266 - 3270
[2] Organocatalytic Enantioselective Mannich-type Addition of 5H-Oxazol-4-ones to Isatin Derived Ketimines
Huang Qiuhong
Li Wenjun
Li Xin
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2022, 43 (08):
[3] Enantioselective Construction of Vicinal Sulfur-functionalized Quaternary and Tertiary Stereocenters via Organocatalytic Michael Addition of 5H-Thiazol-4-ones to 1-Azadienes
Li, Fushuai
Zhang, Chen
Cheng, Yuyu
Jia, Qianfa
Li, Wenjun
Liu, Kun
Li, Pengfei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (08) : 1183 - 1186
[4] Enantioselective construction of 3-substituted 3-amino-2-oxindoles containing an N,N-ketal skeleton via organocatalyzed aza-addition of isatin imines
Zhang, Chen
Shang, Xinye
Cheng, Yuyu
Li, Fushuai
Zhao, Hanhui
Li, Pengfei
Li, Wenjun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (36) : 8374 - 8378
[5] Bis(imidazolidine)pyridine-NiCl2 Catalyst for Nitro-Mannich Reaction of Isatin-Derived N-Boc Ketimines: Asymmetric Synthesis of Chiral 3-Substituted 3-Amino-2-oxindoles
Arai, Takayoshi
Matsumura, Eri
Masu, Hyuma
ORGANIC LETTERS, 2014, 16 (10) : 2768 - 2771

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