Tandem [2+1] cycloaddition-ring expansion of bicyclic Alkenes with tertiary propargylic acetates catalyzed by palladium(II)-Coordinated phosphinous acid

被引:34
|
作者
Bigeault, Julie [1 ]
de Riggi, Innocenzo [1 ]
Gimbert, Yves [2 ]
Giordano, Laurent [1 ]
Buono, Gerard [1 ]
机构
[1] Univ Aix Marseille, ECM, Inst Sci Mol Marseille ISM2, F-13397 Marseille 20, France
[2] Univ Grenoble 1, CNRS, UMR 5250, Dept Chim Mol,ICMG FR 2607, F-38041 Grenoble, France
关键词
palladium; secondary phosphine oxides; tertiary propargylic acetate; bicyclic alkene; tandem reaction;
D O I
10.1055/s-2008-1042919
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Palladium-SPO complex catalyzed the tandem [2+1] cycloaddition-ring expansion of norbornene derivatives with tertiary propargylic acetates to afford bicyclo[3.2.1]octadienes.
引用
收藏
页码:1071 / 1075
页数:5
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共 8 条
  • [1] Platinum(II) - Coordinated phosphinous acid-catalyzed alkylidenecyclopropanation of bicyclic alkenes with terminal alkynes
    Bigeault, Julie
    Giordano, Laurent
    De Riggi, Innocenzo
    Gimbert, Yves
    Buono, Gerard
    [J]. ORGANIC LETTERS, 2007, 9 (18) : 3567 - 3570
  • [2] CpRuCl(PPh3)2-catalyzed cyclopropanation of bicyclic alkenes with tertiary propargylic acetates
    Tenaglia, A
    Marc, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (09): : 3569 - 3575
  • [3] Diastereoselective [4+1] Cycloaddition of Alkenyl Propargylic Tertiary Acetates with CO Catalyzed by [RhCl(CO)2]2
    Zhang, Yanjin
    Zhao, Gang
    Pu, Lin
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (47) : 7026 - 7033
  • [4] [2+1] cycloadditions of terminal alkynes to norbornene derivatives catalyzed by palladium complexes with phosphinous acid ligands
    Bigeault, J
    Giordano, L
    Buono, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (30) : 4753 - 4757
  • [5] Tandem Rh(ii)-catalyzed 1,3-acyloxy migration/intermolecular [2 + 2] cycloaddition of electron-deficient propargylic esters with alkenes and alkynes
    Xu, Zurong
    Zhu, Dong
    Wu, Rui
    Zhu, Shifa
    [J]. Chemical Science, 2024, 16 (01) : 205 - 210
  • [6] Cationic palladium(II) complex-catalyzed [2+2] cycloaddition and tandem cycloaddition-allylic rearrangement of ketene with aldehydes: an improved synthesis of sorbic acid
    Hattori, T
    Suzuki, Y
    Uesugi, O
    Oi, S
    Miyano, S
    [J]. CHEMICAL COMMUNICATIONS, 2000, (01) : 73 - 74
  • [7] One-Pot Synthesis of Indolizines via Sequential Rhodium-Catalyzed [2+1]-Cyclopropanation, Palladium-Catalyzed Ring Expansion, and Oxidation Reactions from Pyridotriazoles and 1,3-Dienes
    Kim, Hyunseok
    Kim, Sanghyuck
    Kim, Jiyeon
    Son, Jeong-Yu
    Baek, Yonghyeon
    Um, Kyusik
    Lee, Phil Ho
    [J]. ORGANIC LETTERS, 2017, 19 (20) : 5677 - 5680
  • [8] Formal asymmetric synthesis of pentalenolactone E and pentalenolactone F -: 1.: Retrosynthesis and π-facial differentiation in palladium-catalyzed and dipolar [3+2]-cycloaddition reactions of bicyclic alkenes:: Evidence for electrostatic control of stereoselectivity
    Rosenstock, B
    Gais, HJ
    Herrmann, E
    Raabe, G
    Binger, P
    Freund, A
    Wedemann, P
    Kruger, C
    Lindner, HJ
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (02) : 257 - 273