Dinuclear Zinc Catalyzed [3+2] Annulation of Benzylideneindolinones Access to CF3-Containing 2,3-Pyrrolidinyl Dispirooxindoles

被引:5
作者
Zhai, Ying-Hui [1 ,2 ]
Guo, Ya-Jun [1 ,2 ]
Du, Si-Si [1 ,2 ]
Wang, Min-Can [1 ,2 ]
Jia, Shi-Kun [1 ,2 ]
Hua, Yuan-Zhao [1 ,2 ]
机构
[1] Zhengzhou Univ, Coll Chem, 100 Sci Rd, Zhengzhou 450000, Henan, Peoples R China
[2] Zhengzhou Univ, Inst Green Catalysis, 100 Sci Rd, Zhengzhou 450000, Henan, Peoples R China
关键词
dinuclear zinc catalyst; 2,3-pyrrolidinyl dispirooxindoles; benzylideneindolinone; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; AZOMETHINE YLIDES; CYCLOADDITION; CONSTRUCTION; FLUORINE;
D O I
10.1002/adsc.202300705
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
This report has realized the catalytic asymmetric [3+2] annulation of benzylideneindolinones with CF3-containing isatin-derived azomethine ylides for the first time, in which the organocatalysis has failed. In the presence of dinuclear zinc catalysts, a series of functionalized 2,3-pyrrolidinyl dispirooxindoles have been synthesized in good yields with excellent stereoselectivity under mild reaction conditions. This protocol can be run on a gram scale and a possible catalytic mechanism is proposed.
引用
收藏
页码:3088 / 3093
页数:6
相关论文
共 48 条
[1]   Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products [J].
Antonchick, Andrey P. ;
Gerding-Reimers, Claas ;
Catarinella, Mario ;
Schuermann, Markus ;
Preut, Hans ;
Ziegler, Slava ;
Rauh, Daniel ;
Waldmann, Herbert .
NATURE CHEMISTRY, 2010, 2 (09) :735-740
[2]   Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line [J].
Arun, Y. ;
Bhaskar, G. ;
Balachandran, C. ;
Ignacimuthu, S. ;
Perumal, P. T. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (06) :1839-1845
[3]   PyBidine/Copper Catalyst: Asymmetric exo′-Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole [J].
Awata, Atsuko ;
Arai, Takayoshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10462-10465
[4]   Stereocontrolled synthesis of highly substituted proline esters via [3+2] cycloaddition between N-metalated azomethine ylides and nitroalkenes.: Origins of the metal effect on the stereochemical outcome [J].
Ayerbe, M ;
Arrieta, A ;
Cossío, FP ;
Linden, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1795-1805
[5]  
Babu A., 2008, CURR CHEM BIOL, V2, P312, DOI DOI 10.2174/187231308785739729
[6]   Strategies for the enantioselective synthesis of spirooxindoles [J].
Ball-Jones, Nicolas R. ;
Badillo, Joseph J. ;
Franz, Annaliese K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) :5165-5181
[7]   Organic fluorine compounds: a great opportunity for enhanced materials properties [J].
Berger, Ricarda ;
Resnati, Giuseppe ;
Metrangolo, Pierangelo ;
Weber, Edwin ;
Hulliger, Juerg .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3496-3508
[8]   Stereoselective synthesis of CF3-containing spirocyclic-oxindoles using N-2,2,2-trifluoroethylisatin ketimines: an update [J].
Borah, Biplob ;
Veeranagaiah, Naveena S. ;
Sharma, Samrita ;
Patat, Mihir ;
Prasad, Madavi S. ;
Pallepogu, Raghavaiah ;
Chowhan, L. Raju .
RSC ADVANCES, 2023, 13 (11) :7063-7075
[9]   Kinetic Resolution of trans-2,3-Aziridinyl Alcohols via Hydroxyl Directed Regio- and Enantioselective Ring Opening Reactions [J].
Chang, Zhe-Ran ;
Du, Si-Si ;
Zhang, Cui ;
Chen, Shuang-Hu ;
Hua, Yuan-Zhao ;
Wang, Min-Can ;
Mei, Guang-Jian ;
Jia, Shi-Kun .
ACS CATALYSIS, 2023, 13 (10) :6873-6878
[10]   Dinuclear zinc catalyzed asymmetric [3+2] spiroannulation for the synthesis of diverse bispirocyclic saccharines [J].
Chen, Shuang-Hu ;
Miao, Yu-Hang ;
Mei, Guang-Jian ;
Hua, Yuan-Zhao ;
Jia, Shi-Kun ;
Wang, Min-Can .
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (18) :5010-5015