A chiral cobalt(II) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines

被引：11
|
作者：
Ma, Baiwei [1 ]
Luo, Weiwei [1 ]
Lin, Lili [1 ]
Liu, Xiaohua [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 29期
基金：
中国国家自然科学基金;
关键词：
DIELS-ALDER REACTION; ENANTIOSELECTIVE SYNTHESIS; DIETHYL AZODICARBOXYLATE; 5-ALKOXYOXAZOLES; ALDEHYDES; OXAZOLES; 4-PHENYL-3H-1,2,4-TRIAZOLE-3,5(4H)-DIONE; AMINATION; LIGANDS; ESTERS;
D O I：
10.1039/c7cc01278k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly efficient catalytic asymmetric formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N, N'-dioxide/Co(BF4)(2)center dot 6H(2)O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained in moderate to excellent yields (70-99%) with excellent enantioselectivities (82-98% ee).
引用
收藏
页码：4077 / 4079
页数：3
相关论文
共 50 条
  • [1] Enantioselective synthesis of 1,2,4-triazolines by chiral iron(II)-complex catalyzed cyclization of α-isocyano esters and azodicarboxylates
    Wang, Min
    Liu, Xiaohua
    He, Peng
    Lin, Lili
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2013, 49 (25) : 2572 - 2574
  • [2] Enantioselective synthesis of 1,2,4-triazolines catalyzed by a cinchona alkaloid-derived organocatalyst
    Shao, Qian
    Chen, Jiean
    Tu, Meihua
    Piotrowski, David W.
    Huang, Yong
    CHEMICAL COMMUNICATIONS, 2013, 49 (94) : 11098 - 11100
  • [3] Synthesis of 1,2,4-Triazolines and Triazoles Utilizing Oxazolones
    Saleem, Rahman Shah Zaib
    Tepe, Jetze J.
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (12) : 4330 - 4332
  • [4] Synthesis of 1,2,4-Triazolines: Base-Catalyzed Hydrazination/Cyclization Cascade of α-Isocyano Esters and Amides
    Monge, David
    Jensen, Kim L.
    Marin, Irene
    Jorgensen, Karl Anker
    ORGANIC LETTERS, 2011, 13 (02) : 328 - 331
  • [5] Chiral Phosphoric Acid Catalyzed [3+2] Cycloaddition and Tandem Oxidative [3+2] Cycloaddition: Asymmetric Synthesis of Substituted 3-Aminodihydrobenzofurans
    Gelis, Coralie
    Bekkaye, Mathieu
    Lebee, Clement
    Blanchard, Florent
    Masson, Geraldine
    ORGANIC LETTERS, 2016, 18 (14) : 3422 - 3425
  • [6] Chiral nickel(II) complex catalyzed asymmetric (3+2) cycloaddition of α-diazo pyrazoleamides with 2-siloxy-1-alkenes
    Yang, Wei
    Yang, Zhendong
    Chen, Long
    Lu, Yican
    Zhang, Cefei
    Su, Zhishan
    Liu, Xiaohua
    Feng, Xiaoming
    CHINESE CHEMICAL LETTERS, 2023, 34 (04)
  • [7] Organocatalytic synthesis of enantioenriched 1,2,4-triazolines containing a chiral quaternary carbon center
    Zhang, Li-Jun
    Zhang, Si-Xiang
    Fu, Li-Na
    Li, Xiao-Yun
    Guo, Qi-Xiang
    RSC ADVANCES, 2017, 7 (30): : 18714 - 18717
  • [8] Cinchona Alkaloid Squaramide Catalyzed Enantioselective Hydrazination/Cyclization Cascade Reaction of α-Isocyanoacetates and Azodicarboxylates: Synthesis of Optically Active 1,2,4-Triazolines
    Zhao, Mei-Xin
    Bi, Hong-Lei
    Zhou, Hao
    Yang, Hui
    Shi, Min
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) : 9377 - 9382
  • [9] New 1,3-dipolar cycloaddition/dehydrogenation of azomethines ylides and azodicarboxylates: direct and effective construction of unsaturated 1,2,4-triazolines
    Wang, Qi-Lin
    Fu, Ji-Ya
    Peng, Lin
    Yang, Qing-Chuan
    Jia, Li-Na
    Luo, Xi-Ya
    Gui, Yong-Yuan
    Tian, Fang
    Wang, Wen
    Xu, Xiao-Ying
    Wang, Li-Xin
    TETRAHEDRON LETTERS, 2012, 53 (24) : 2985 - 2988
  • [10] Enantioselective synthesis of chiral phosphonylated 2,3-dihydrofurans by copper catalyzed asymmetric formal [3+2] cycloaddition of propargylic esters with β-keto phosphonates
    Chen, Xiushuai
    Hou, Chuanjin
    Li, Qing
    Liu, Yanjun
    Yang, Ruifeng
    Hu, Xiangping
    CHINESE JOURNAL OF CATALYSIS, 2016, 37 (08) : 1389 - 1395
12345