Phosphine-Catalyzed Substitution of Allenoates with Oxindoles: An Approach to 3-Allenic or 3-Dienoic Oxindoles

被引:0
作者
Yang, Ze-ren [1 ]
Gui, Hou-ze [2 ,3 ]
Shi, Min [1 ,2 ,3 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] East China Univ Sci & Technol, Key Lab Adv Mat, 130 Mei Long Rd, Shanghai 200237, Peoples R China
[3] East China Univ Sci & Technol, Inst Fine Chem, 130 Mei Long Rd, Shanghai 200237, Peoples R China
来源
CHEMISTRYSELECT | 2021年 / 6卷 / 36期
基金
中国国家自然科学基金;
关键词
Organocatalysis; nucleophilic substitution; allenes; ENANTIOSELECTIVE GAMMA-ADDITION; 3-ISOTHIOCYANATO OXINDOLES; ALLENES; ANNULATION; 2,3-BUTADIENOATES; CYCLOADDITION; CONSTRUCTION; NUCLEOPHILES; HETEROCYCLES; KETIMINES;
D O I
10.1002/slct.202102930
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for substitution of allenoate using oxindoles as nucleophilic reagents has been disclosed in this paper upon phosphine catalysis under mild conditions to afford 3-allenic or 3-dienoic oxindoles in moderate to good yields depending on the substituent at the aromatic ring of oxindole. According to the previous works, the plausible reaction mechanisms have been proposed.
引用
收藏
页码:9709 / 9713
页数:5
相关论文
共 47 条
[21]   Use of a New Spirophosphine To Achieve Catalytic Enantioselective [4+1] Annulations of Amines with Allenes To Generate Dihydropyrroles [J].
Kramer, Soren ;
Fu, Gregory C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (11) :3803-3806
[22]  
Li E., 2016, ANGEW CHEM, V128, P11763
[23]   Bifunctional-Phosphine-Catalyzed Sequential Annulations of Allenoates and Ketimines: Construction of Functionalized Poly-heterocycle Rings [J].
Li, Erqing ;
Jin, Hongxing ;
Jia, Penghao ;
Dong, Xuelin ;
Huang, You .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (38) :11591-11594
[24]   Phosphine-Catalyzed Sequential [2+3] and [3+2] Annulation Domino Reaction of γ-Benzyl-Substituted Allenoates with α,β-Unsaturated Ketimines To Construct aza-Bicyclo[3,3,0]octane Derivatives [J].
Li, Erqing ;
Jia, Penghao ;
Ling, Ling ;
Huang, You .
ACS CATALYSIS, 2014, 4 (02) :600-603
[25]   Enantioselective Synthesis of Chiral Allenoates by Guanidine-Catalyzed Isomerization of 3-Alkynoates [J].
Liu, Hongjun ;
Leow, Dasheng ;
Huang, Kuo-Wei ;
Tan, Choon-Hong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (21) :7212-+
[26]   Stereodivergent Synthesis of N-Heterocycles by Catalyst-Controlled, Activity-Directed Tandem Annulation of Diazo Compounds with Amino Alkynes [J].
Liu, Kai ;
Zhu, Chenghao ;
Min, Junxiang ;
Peng, Shiyong ;
Xu, Guangyang ;
Sun, Jiangtao .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) :12962-12967
[27]   Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes [J].
Liu, Lu ;
Ward, Robert M. ;
Schomaker, Jennifer M. .
CHEMICAL REVIEWS, 2019, 119 (24) :12422-12490
[28]   Phosphine-Catalyzed [4+2] Annulation of Allenoate with Sulfamate-Derived Cyclic 'mines: A Reaction Mode Involving γ′-Carbon of α-Substituted Allenoate [J].
Mao, Biming ;
Shi, Wangyu ;
Liao, Jianning ;
Liu, Honglei ;
Zhang, Cheng ;
Guo, Hongchao .
ORGANIC LETTERS, 2017, 19 (23) :6340-6343
[29]   Asymmetric Organocatalysis in Fullerenes Chemistry: Enantioselective Phosphine-catalyzed Cycloaddition of Allenoates onto C60 [J].
Marco-Martinez, Juan ;
Marcos, Vanesa ;
Reboredo, Silvia ;
Filippone, Salvatore ;
Martin, Nazario .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (19) :5115-5119
[30]   Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts [J].
Miro, Javier ;
Gensch, Tobias ;
Ellwart, Mario ;
Han, Seo-Jung ;
Lin, Hsin-Hui ;
Sigman, Matthew S. ;
Toste, F. Dean .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (13) :6390-6399