Palladium catalyzed cascade umpolung allylation/acetalation for the construction of quaternary 3-amino oxindoles

被引：3

作者：

Sun, Xi-Shang ^{[1
]}

Chang, Xin ^{[1
]}

Shi, Li-Min ^{[1
]}

Wang, Zuo-Fei ^{[1
]}

Wei, Liang ^{[1
]}

Wang, Chun-Jiang ^{[1
,2
]}

机构：

[1] Wuhan Univ, Engn Res Ctr Organosilicon Cpds & Mat, Coll Chem & Mol Sci, Minist Educ, Wuhan 430072, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 230021, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2021年 / 57卷 / 64期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; MARINE ALKALOIDS; NATURAL-PRODUCTS; ALLENES; CYCLOADDITION; CYCLIZATION; ALLYLATION; ANTAGONIST; ARYLATION;

D O I：

10.1039/d1cc03075b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein we reported a highly diastereoselective synthesis of quaternary 3-amino oxindoles bearing an acetal unit via a palladium catalyzed three-component cascade umpolung allylation/acetalation process. An array of 3-amino 3-allyl oxindoles incorporating diversified functional groups were prepared in good yields with exclusive diastereoselectivities. Further investigation demonstrated that the current method could also be extended to cascade umpolung allenylation/acetalation.

引用

页码：7958 / 7961

页数：4

共 50 条

[31] Palladium-catalyzed enantioselective umpolung allylation of amido-tethered allylic carbonates with isatin-derived ketimines
Wang, Lan
Lu, Mengxi
Li, Kuan
Yang, Sen
Wang, Lei
Guo, Hongchao
CHEMICAL COMMUNICATIONS, 2024, 60 (27) : 3729 - 3732
[32] Asymmetric Michael Addition of Oxindoles to Allenoate Catalyzed by N-Acyl Aminophosphine: Construction of Functionalized Oxindoles with Quaternary Stereogenic Center
Chen, Jinhao
Cai, Yuepeng
Zhao, Gang
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 359 - 363
[33] Stereocontrolled Construction of 3,4-Dihydrocoumarin Scaffolds with a Quaternary Amino Acid Moiety via Chiral Squaramide-Catalyzed Cascade Michael Addition/Lactonization Reaction
Wang, Yuehua
Pan, Jianping
Jiang, Rongrong
Wang, Youming
Zhou, Zhenghong
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (02) : 195 - 200
[34] Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes
Jiang, Zhiwei
Hou, Longlei
Ni, Chunjie
Chen, Jiangfei
Wang, Dong
Tong, Xiaofeng
CHEMICAL COMMUNICATIONS, 2017, 53 (30) : 4270 - 4273
[35] Construction of multifunctional heterocycles bearing aza-quaternary carbons by titanocene-catalyzed umpolung reactions
Cheng, Jiang-Tao
Zheng, Xiao
Huang, Pei-Qiang
TETRAHEDRON, 2019, 75 (12) : 1612 - 1623
[36] Photoinduced Alkyl/Aryl Radical Cascade for the Synthesis of Quaternary CF3-Containing Oxindoles and Indoline Alkaloids
Shaw, Ranjay
Sihag, Naveen
Jain, Swati
Sharma, Ruchi
Yadav, M. Ramu
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5652 - 5660
[37] Palladium-Catalyzed Asymmetric Desymmetrization for the Simultaneous Construction of Chiral Phosphorus and Quaternary Carbon Stereocenters
Zhou, Hengrui
Xue, Yiji
Zhou, Xiang
Yao, Hequan
Lin, Aijun
ORGANIC LETTERS, 2024, 26 (28) : 5934 - 5939
[38] Calcium-Catalyzed Asymmetric Synthesis of 3-Tetrasubstituted Oxindoles: Efficient Construction of Adjacent Quaternary and Tertiary Chiral Centers
Shimizu, Shota
Tsubogo, Tetsu
Xu, Pengyu
Kobayashi, Shu
ORGANIC LETTERS, 2015, 17 (08) : 2006 - 2009
[39] In(OTf)3-Catalyzed Cascade Cyclization for Construction of Oxatricyclic Compounds
Bao, Wenli
Tao, Yezi
Cheng, Jiangqun
Huang, Junrong
Cao, Jingming
Zhang, Mengxun
Ye, Weijian
Wang, Bo
Li, Yang
Zhu, Lizhi
Lee, Chi-Sing
ORGANIC LETTERS, 2018, 20 (24) : 7912 - 7915
[40] Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of 3-substituted oxindoles
Qian, Zi-Qing
Zhou, Feng
Du, Tai-Ping
Wang, Bo-Lun
Ding, Miao
Zhao, Xiao-Li
Zhou, Jian
CHEMICAL COMMUNICATIONS, 2009, (44) : 6753 - 6755

← 1 2 3 4 5 →