High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

被引:58
|
作者
Johns, Adam M. [1 ]
Ahmed, Tonia S. [2 ]
Jackson, Bradford W. [1 ]
Grubbs, Robert H. [2 ]
Pederson, Richard L. [1 ]
机构
[1] CALTECH, Arnold & Mabel Beckman Labs Chem Synth, Div Chem & Chem Engn, Pasadena, CA 91125 USA
[2] Materia Inc, Pasadena, CA 91107 USA
基金
美国国家科学基金会;
关键词
RING-OPENING/CROSS-METATHESIS; TERMINAL OLEFINS; CATALYST; ALKYNES; MECHANISM; COMPLEX; HOMODIMERIZATION; HYDROGENATION; ETHENOLYSIS; DFT;
D O I
10.1021/acs.orglett.6b00031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first kinetically controlled, highly trans selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereo chemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans olefins and between a trans olefin and a terminal olefin. Additionally, new stereoretentive catalysts have been synthesized for improved reactivity.
引用
收藏
页码:772 / 775
页数:4
相关论文
共 50 条
  • [1] Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts
    Ahmed, Tonia S.
    Montgomery, T. Patrick
    Grubbs, Robert H.
    [J]. CHEMICAL SCIENCE, 2018, 9 (14) : 3580 - 3583
  • [2] Ruthenium-catalyzed olefin cross-metathesis with tetrafluoroethylene
    Takahira, Yusuke
    Usuda, Tsukasa
    Morizawa, Yoshitomi
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [3] Reactivation of a Ruthenium-Based Olefin Metathesis Catalyst
    Tabari, Daniel S.
    Tolentino, Daniel R.
    Schrodi, Yann
    [J]. ORGANOMETALLICS, 2013, 32 (01) : 5 - 8
  • [4] Recent advances in ruthenium-based olefin metathesis
    Ogba, O. M.
    Warner, N. C.
    O'Leary, D. J.
    Grubbs, R. H.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (12) : 4510 - 4544
  • [5] Selectivity in terminal olefin cross-metathesis reactions.
    Bussmann, DA
    Bergset, JM
    Chatterjee, AK
    O'Leary, DJ
    Grubbs, RH
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U341 - U341
  • [6] Cross-Metathesis of Vinyl Halides. Scope and Limitations of Ruthenium-Based Catalysts
    Macnaughtan, Marisa L.
    Gary, J. Brannon
    Gerlach, Deidra L.
    Johnson, Marc J. A.
    Kampf, Jeff W.
    [J]. ORGANOMETALLICS, 2009, 28 (09) : 2880 - 2887
  • [7] Ruthenium-based olefin metathesis: Insight into catalyst decomposition
    Lavoie, Gino
    Larocque, Timothy
    Badaj, Anna
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [8] Functional group diversity by ruthenium-catalyzed olefin cross-metathesis
    Toste, FD
    Chatterjee, AK
    Grubbs, RH
    [J]. PURE AND APPLIED CHEMISTRY, 2002, 74 (01) : 7 - 10
  • [9] Ruthenium-Based Olefin Metathesis Catalysts Derived from Alkynes
    Lozano-Vila, Ana M.
    Monsaert, Stijn
    Bajek, Agata
    Verpoort, Francis
    [J]. CHEMICAL REVIEWS, 2010, 110 (08) : 4865 - 4909
  • [10] Ruthenium-Catalyzed Olefin Cross-Metathesis with Tetrafluoroethylene and Analogous Fluoroolefins
    Takahira, Yusuke
    Morizawa, Yoshitomi
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (22) : 7031 - 7034