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
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
  • [21] Variation of the Sterical Properties of the N-Heterocyclic Carbene Coligand in Thermally Triggerable Ruthenium-Based Olefin Metathesis Precatalysts/Initiators
    Pump, Eva
    Leitgeb, Anita
    Kozlowska, Anna
    Torvisco, Ana
    Falivene, Laura
    Cavallo, Luigi
    Grela, Karol
    Slugovc, Christian
    ORGANOMETALLICS, 2015, 34 (22) : 5383 - 5392
  • [22] Highly active ruthenium catalysts for olefin metathesis: The synergy of N-heterocyclic carbenes and coordinatively labile ligands
    Weskamp, T
    Kohl, FJ
    Hieringer, W
    Gleich, D
    Herrmann, WA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1999, 38 (16) : 2416 - 2419
  • [23] Tuning of ruthenium N-heterocyclic carbene catalysts for ATRP
    Delaude, L
    Delfosse, S
    Richel, A
    Demonceau, A
    Noels, AF
    CHEMICAL COMMUNICATIONS, 2003, (13) : 1526 - 1527
  • [24] Concise route to highly reactive ruthenium metathesis catalysts containing a labile donor and an N-heterocyclic carbene (NHC) ligand
    Conrad, JC
    Yap, GPA
    Fogg, DE
    ORGANOMETALLICS, 2003, 22 (10) : 1986 - 1988
  • [25] Highly Reactive Cationic Molybdenum Alkylidyne N-Heterocyclic Carbene Catalysts for Alkyne Metathesis
    Groos, Jonas
    Hauser, Philipp M.
    Koy, Maximilian
    Frey, Wolfgang
    Buchmeiser, Michael R.
    ORGANOMETALLICS, 2021, 40 (08) : 1178 - 1184
  • [26] Ruthenium olefin metathesis catalysts with 4-membered N-heterocyclic carbene ligands.
    Despagnet-Ayoub, E
    Grubbs, RH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U876 - U876
  • [27] Ruthenium-arene catalysts bearing N-heterocyclic carbene ligands for olefin cyclopropanation and metathesis
    Meret, Michael
    Maj, Anna M.
    Demonceau, Albert
    Delaude, Lionel
    MONATSHEFTE FUR CHEMIE, 2015, 146 (07): : 1099 - 1105
  • [28] Chiral-at-Ruthenium Catalysts with Mixed Normal and Abnormal N-Heterocyclic Carbene Ligands
    Winterling, Erik
    Ivlev, Sergei
    Meggers, Eric
    ORGANOMETALLICS, 2021, 40 (08) : 1148 - 1155
  • [29] Kinetics and Mechanism of Isocyanide-Promoted Carbene Insertion into the Aryl Substituent of an N-Heterocyclic Carbene Ligand in Ruthenium-Based Metathesis Catalysts (vol 36, pg 3043, 2017)
    Griffiths, Justin R.
    Hofman, Elan J.
    Keister, Jerome B.
    Diver, Steven T.
    ORGANOMETALLICS, 2018, 37 (15) : 2653 - 2653
  • [30] Synthesis of chiral chelating N-heterocyclic carbene complexes of ruthenium
    Marshall, C
    Ward, MF
    Harrison, WTA
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) : 3970 - 3975