Iron- or Cobalt-Catalyzed Nazarov Cyclization: Asymmetric Reaction and Tandem Cyclization-Fluorination Reaction

被引:67
|
作者
Kawatsura, Motoi [1 ]
Kajita, Koji [1 ]
Hayase, Shuichi [1 ]
Itoh, Toshiyuki [1 ]
机构
[1] Tottori Univ, Grad Sch Engn, Dept Chem & Biotechnol, Tottori 6808552, Japan
关键词
iron catalyst; cobalt catalyst; Nazarov cyclization; fluorination; SUBSTITUTED DIVINYL KETONES; STEREOSELECTIVE-SYNTHESIS; OXYALLYL INTERMEDIATE; PYRROLE DERIVATIVES; EFFICIENT CATALYSIS; MICHAEL ADDITION; ACID; (E)-3-CROTONOYLOXAZOLIDIN-2-ONE; REARRANGEMENT; CONSTRUCTION;
D O I
10.1055/s-0029-1219782
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We succeeded in demonstrating the iron- or cobalt-catalyzed asymmetric Nazarov cyclization of divinyl ketones using iron or cobalt catalysts, which were prepared from Co(ClO(4))(2)center dot 6H(2)O, Fe(ClO(4))(2)center dot 6H(2)O, or Fe(OTf)(2) with a chiral pybox-type ligand. Furthermore, we found that Fe(OTf)(2) effectively catalyzed the tandem Nazarov cyclization-fluorination reaction of divinyl ketones.
引用
收藏
页码:1243 / 1246
页数:4
相关论文
共 50 条
  • [1] Enantioselective Cobalt-Catalyzed Sequential Nazarov Cyclization/Electrophilic Fluorination: Access to Chiral α-Fluorocyclopentenones
    Zhang, Heyi
    Cheng, Biao
    Lu, Zhan
    ORGANIC LETTERS, 2018, 20 (13) : 4028 - 4031
  • [2] Iron- and Cobalt-Catalyzed Asymmetric Hydrofunctionalization of Alkenes and Alkynes
    Guo, Jun
    Cheng, Zhaoyang
    Chen, Jianhui
    Chen, Xu
    Lu, Zhan
    ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (11) : 2701 - 2716
  • [3] Cobalt-catalyzed tandem radical cyclization and cross-coupling reaction: Its application to benzyl-substituted heterocycles
    Wakabayashi, K
    Yorimitsu, H
    Oshima, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (22) : 5374 - 5375
  • [4] Cobalt-Catalyzed Cyclization/Hydrosilylation Reaction of 1,6-Diynes Enabled by an Oxidative Cyclization-Hydrosilylation Mechanism
    Dong, Jiaxing
    Leng, Xuebing
    Wang, Dongyang
    Deng, Liang
    ACS CATALYSIS, 2024, 14 (06) : 4001 - 4007
  • [5] Mechanistic investigation of Nazarov cyclization reaction catalyzed by palladium(0) complexes
    Atesin, Tulay
    Tius, Marcus
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [6] Cobalt-catalyzed isocyanide insertion cyclization to dihydrobenzoimidazotriazins
    Ahmadi, Fereshteh
    Mirzaei, Peiman
    Bazgir, Ayoob
    TETRAHEDRON LETTERS, 2017, 58 (45) : 4281 - 4284
  • [7] Cobalt-Catalyzed Cyclization of Unsaturated N-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction
    Fischer, David M.
    Balkenhohl, Moritz
    Carreira, Erick M.
    JACS AU, 2022, 2 (05): : 1071 - 1077
  • [8] Cobalt-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes with Pinacolborane
    Yu, Songjie
    Wu, Caizhi
    Ge, Shaozhong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (19) : 6526 - 6529
  • [9] Pentannulation Reaction by Tandem Gold(I)-Catalyzed Propargyl Claisen Rearrangement/Nazarov Cyclization of Enynyl Vinyl Ethers
    Rinaldi, Antonia
    Petrovic, Martina
    Magnolfi, Stefano
    Scarpi, Dina
    Occhiato, Ernesto G.
    ORGANIC LETTERS, 2018, 20 (15) : 4713 - 4717
  • [10] Asymmetric Cobalt-Catalyzed Regioselective Hydrosilylation/Cyclization of 1,6-Enynes
    You, Yang'en
    Ge, Shaozhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (21) : 12046 - 12052