Cation radical [3+2] cycloaddition of chalcone epoxides:: A facile synthesis of highly substituted tetrahydrofurans

被引:30
|
作者
Huo, CD [1 ]
Jia, XD [1 ]
Zhang, W [1 ]
Yang, L [1 ]
Lü, JM [1 ]
Liu, ZL [1 ]
机构
[1] Lanzhou Univ, Natl Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
关键词
cation radical; cycloaddition; epoxides; tetrahydrofurans;
D O I
10.1055/s-2003-44966
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloaddition of electron-rich chalcone epoxides with electron-rich olefins was efficiently catalyzed by tris(4-bromophenyl)aminium hexachloroantimonate producing poly-substituted tetrahydrofuran derivatives in high yield.
引用
收藏
页码:251 / 254
页数:4
相关论文
共 50 条
  • [31] The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates
    Barros, Maria Teresa
    Faisca Phillips, Ana Maria
    [J]. TETRAHEDRON-ASYMMETRY, 2010, 21 (21-22) : 2746 - 2752
  • [32] A facile three-component [3+2]-cycloaddition for the regioselective synthesis of highly functionalised dispiropyrrolidines acting as antimycobacterial agents
    Wei, Ang Chee
    Ali, Mohamed Ashraf
    Yoon, Yeong Keng
    Ismail, Rusli
    Choon, Tan Soo
    Kumar, Raju Suresh
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) : 1383 - 1386
  • [33] Facile synthesis of 3-trimethylsilylindazoles by [3+2]cycloaddition reaction of lithium trimethylsilyldiazomethane with benzynes
    Shoji, Y
    Hari, Y
    Aoyama, T
    [J]. TETRAHEDRON LETTERS, 2004, 45 (08) : 1769 - 1771
  • [34] A highly diastereoselective approach to tetrahydrofurans via [3+2] cycloadditions of silylmethyl-substituted cyclopropanes with aldehydes and ketones
    Gupta, Archana
    Yadav, Veejendra K.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (46) : 8043 - 8047
  • [35] Formal [3+2] Cycloaddition Reactions of Electron-Rich Aryl Epoxides with Alkenes under Lewis Acid Catalysis Affording Tetrasubstituted Tetrahydrofurans
    Macias-Villamizar, Victor E.
    Cuca-Suarez, Luis
    Rodriguez, Santiago
    Gonzalez, Florenci, V
    [J]. MOLECULES, 2020, 25 (03):
  • [36] Pd-Catalyzed (3+2) Heterocycloadditions between Alkylidenecyclopropanes and Carbonyls: Straightforward Assembly of Highly Substituted Tetrahydrofurans
    Verdugo, Felipe
    da Concepcion, Eduardo
    Rodino, Ricardo
    Calvelo, Martin
    Mascarenas, Jose L.
    Lopez, Fernando
    [J]. ACS CATALYSIS, 2020, 10 (14) : 7710 - 7718
  • [37] Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
    Chen, Weiliang
    Xia, Yong
    Lin, Lili
    Yuan, Xiao
    Guo, Songsong
    Liu, Xiaohua
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (43) : 15104 - 15107
  • [38] A facile and efficient synthesis of highly functionalised 3,3′-dispiropyrrolidine- and 3,3′-dispiropyrrolizidine bisoxindoles via [3+2] cycloaddition
    Shanmugam, Ponnusamy
    Viswambharan, Baby
    Selvakumar, Kodirajan
    Madhavan, Suchithra
    [J]. TETRAHEDRON LETTERS, 2008, 49 (16) : 2611 - 2615
  • [39] Highly Diastereo- and Enantioselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and α,β-Unsaturated Ketones
    Suo, Jia-Jia
    Du, Juan
    Liu, Qing-Rong
    Chen, Di
    Ding, Chang-Hua
    Peng, Qian
    Hou, Xue-Long
    [J]. ORGANIC LETTERS, 2017, 19 (24) : 6658 - 6661
  • [40] Scope of the formal [3+2] cycloaddition for the synthesis of substituted 3-arylindanes and related compounds
    Lantano, Beatriz
    Aguirre, Jose Manuel
    Ugliarolo, Esteban Ariel
    Benegas, Maria Laura
    Moltrasio, Graciela Yolanda
    [J]. TETRAHEDRON, 2008, 64 (18) : 4090 - 4102