Highly Active Chiral Ruthenium-Based Metathesis Catalysts through a Monosubstitution in the N-Heterocyclic Carbene

被引：66
作者：
Tiede, Sascha [1 ]
Berger, Anke [1 ]
Schlesiger, David [1 ]
Rost, Daniel [1 ]
Luehl, Anja [1 ]
Blechert, Siegfried [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 23期
关键词：
amino acids; asymmetric catalysis; N-heterocyclic carbenes; olefin metathesis; ruthenium; RING-OPENING/CROSS-METATHESIS; ASYMMETRIC OLEFIN METATHESIS; EFFICIENT ENANTIOSELECTIVE SYNTHESIS; ALKYLIDENE COMPLEXES; ALLYLIC ALKYLATION; NHC-BACKBONE; LIGANDS; DEACTIVATION; ACTIVATION;
D O I：
10.1002/anie.201000940
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equotion Present) Single (substitution) is better: New chiral ruthenium metathesis (pre)catalysts with a monosubstituted carbon atom in the N-heterocyclic carbene ligand are highly stable in solution, initiate easily, show very high enantioselectivity and excellent E selectivity in asymmetric ring-opening cross-metathesis (see scheme).© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：3972 / 3975
页数：4
相关论文
共 50 条
  • [1] Ruthenium-Based Olefin Metathesis Catalysts Bearing N-Heterocyclic Carbene Ligands
    Samojlowicz, Cezary
    Bieniek, Michal
    Grela, Karol
    CHEMICAL REVIEWS, 2009, 109 (08) : 3708 - 3742
  • [2] Ligand-Promoted Carbene Insertion into the Aryl Substituent of an N-Heterocyclic Carbene Ligand in Ruthenium-Based Metathesis Catalysts
    Galan, Brandon R.
    Pitak, Mateusz
    Gembicky, Milan
    Keister, Jerome B.
    Diver, Steven T.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (19) : 6822 - 6832
  • [3] Comparative investigation of ruthenium-based metathesis catalysts bearing N-heterocyclic carbene (NHC) ligands
    Fürstner, A
    Ackermann, L
    Gabor, B
    Goddard, R
    Lehmann, CW
    Mynott, R
    Stelzer, F
    Thiel, OR
    CHEMISTRY-A EUROPEAN JOURNAL, 2001, 7 (15) : 3236 - 3253
  • [4] Ruthenium-based olefin metathesis catalysts coordinated with unsymmetrical N-heterocyclic carbene ligands: Synthesis, structure, and catalytic activity
    Vougioukalakis, Georgios C.
    Grubbs, Robert H.
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (25) : 7545 - 7556
  • [5] Kinetics and Mechanism of Isocyanide-Promoted Carbene Insertion into the Aryl Substituent of an N-Heterocyclic Carbene Ligand in Ruthenium-Based Metathesis Catalysts
    Griffiths, Justin R.
    Hofman, Elan J.
    Keister, Jerome B.
    Diver, Steven T.
    ORGANOMETALLICS, 2017, 36 (16) : 3043 - 3052
  • [6] Ruthenium Olefin Metathesis Catalysts Bearing a Macrocyclic N-Heterocyclic Carbene Ligand: Improved Stability and Activity
    Kosnik, Wioletta
    Lichosyt, Dawid
    Sniezek, Marcin
    Janaszkiewicz, Angelika
    Wozniak, Krzysztof
    Malinska, Maura
    Trzaskowski, Bartosz
    Kajetanowicz, Anna
    Grela, Karol
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (24)
  • [7] Electronic effects in mixed N-heterocyclic carbene/phosphite indenylidene ruthenium metathesis catalysts
    Bidal, Yannick D.
    Urbina-Blanco, Cesar A.
    Poater, Albert
    Cordes, David B.
    Slawin, Alexandra M. Z.
    Cavallo, Luigi
    Cazin, Catherine S. J.
    DALTON TRANSACTIONS, 2019, 48 (30) : 11326 - 11337
  • [8] Exploring new achievements in olefin metathesis catalysts Part 1-Highlights on N-Heterocyclic carbene ruthenium complexes
    Dragutan, Valerian
    Dragutan, Ileana
    Delaude, Lionel
    Demonceau, Albert
    CHIMICA OGGI-CHEMISTRY TODAY, 2009, 27 (03) : 9 - 12
  • [9] Rapid Decomposition of Olefin Metathesis Catalysts by a Truncated N-Heterocyclic Carbene: Efficient Catalyst Quenching and N-Heterocyclic Carbene Vinylation
    Rufh, Stephanie A.
    Goudreault, Alexandre Y.
    Foscato, Marco
    Jensen, Vidar R.
    Fogg, Deryn E.
    ACS CATALYSIS, 2018, 8 (12): : 11822 - 11826
  • [10] Ruthenium Ollefin Metathesis Catalysts Bearing Carbohydrate-Based N-Heterocyclic Carbenes
    Keitz, Benjamin K.
    Grubbs, Robert H.
    ORGANOMETALLICS, 2010, 29 (02) : 403 - 408
12345