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Synthesis of Cyclic Enol Ethers via Molybdenum Alkylidene‐Catalyzed Ring‐Closing Metathesis.ChemInform, 26
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Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans by an Allyl Silane Metathesis - Nucleophilic Addition SequenceSynlett, 1997
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Alois Fürstner, Karol Grela (2000)
Ringschlussmetathese von Alkinen: Anwendung auf die stereoselektive Totalsynthese von Prostaglandin‐E2‐1,15‐LactonAngewandte Chemie, 112
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Effects of Olefin Substitution on the Ring-Closing Metathesis of Dienes.The Journal of organic chemistry, 62 21
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Total Synthesis and Structural Refinement of the Cyclic Tripyrrole Pigment Nonylprodigiosin.The Journal of organic chemistry, 64 22
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Cleavage of Styrene Derivatives from a Solid Support by Ring Closing Olefin MetathesisSynlett, 1997
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Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis ActivityJournal of the American Chemical Society, 118
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Ring Closing Alkyne Metathesis. Comparative Investigation of Two Different Catalyst Systems and Application to the Stereoselective Synthesis of Olfactory Lactones, Azamacrolides, and the Macrocyclic Perimeter of the Marine Alkaloid Nakadomarin AJournal of the American Chemical Society, 121
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A convenient method for removing all highly-colored byproducts generated during olefin metathesis reactionsOrganic letters, 2 9
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M. Crimmins, A. Choy (1999)
An Asymmetric Aldol−Ring-Closing Metathesis Strategy for the Enantioselective Construction of Oxygen Heterocycles: An Efficient Approach to the Enantioselective Synthesis of (+)-LaurencinJournal of the American Chemical Society, 121
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Jerome Wong, P. Lacombe, C. Sturino (1999)
A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogatesTetrahedron Letters, 40
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Connecting Directed Ortho Metalation and Olefin Metathesis Strategies. Benzene-Fused Multiring-Sized Oxygen Heterocycles. First Syntheses of Radulanin A and HeliananeJournal of Organic Chemistry, 63
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Synthesis of Novel Unsaturated Bicyclic Lactams by Ring-Closing MetathesisSynlett, 1999
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Michele Cucullu, Chunbang Li, S. Nolan, S. Nguyen, R. Grubbs (1998)
THERMOCHEMICAL INVESTIGATION OF PHOSPHINE LIGAND SUBSTITUTION REACTIONS INVOLVING TRANS-(PR3)2CL2RU=CH-CH-CPH2 COMPLEXESOrganometallics, 17
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S. Hansen, F. Rominger, M. Metz, P. Hofmann (1999)
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Thomas Kirkland, D. Lynn, R. Grubbs (1998)
Ring-Closing Metathesis in Methanol and WaterJournal of Organic Chemistry, 63
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A. Fürstner, H. Szillat, B. Gabor, R. Mynott (1998)
Platinum- and Acid-Catalyzed Enyne Metathesis Reactions: Mechanistic Studies and Applications to the Syntheses of Streptorubin B and MetacycloprodigiosinJournal of the American Chemical Society, 120
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Proximate, syn‐Periplanar Diazene/Diazene(di)oxy, Diazeneoxy/Diazene(di)oxy, and Diazenedioxy/Diazenedioxy Skeletons: Syntheses, [2+2]Photocycloadditions, MetathesisEuropean Journal of Organic Chemistry, 2000
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W. Goldring, L. Weiler (1999)
Cytotoxic alkaloids motuporamines A-C: synthesis and structural verification.Organic letters, 1 9
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Roland Stragies, S. Blechert* (1999)
Total synthesis of (−)-halosaline by a ruthenium-catalyzed ring rearrangementTetrahedron, 55
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A. Fürstner, A. Hill, Monika Liebl, J. Wilton‐Ely (1999)
Coordinatively unsaturated ruthenium allenylidene complexes: highly effective, well defined catalysts for the ring-closure metathesis of α,ω-dienes and dienynesChemical Communications
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Daisy Joe, L. Overman (1997)
An unexpected product arising from metal alkylidene mediated ring-closing diene metathesisTetrahedron Letters, 38
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B. Fink, P. Kym, J. Katzenellenbogen (1998)
Design, Synthesis, and Conformational Analysis of a Proposed Type I β-Turn MimicJournal of the American Chemical Society, 120
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Alkene metathesis in the synthesis of novel β-lactamsChemical Communications
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C. Baylon, M. Heck, C. Mioskowski (1999)
Bis Ring Closing Olefin Metathesis for the Synthesis of Unsaturated Polycyclic Ethers. O-Membered Ring Cyclization in Favor of C-Membered Ring Cyclization.The Journal of organic chemistry, 64 9
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T. Nishioka, Y. Iwabuchi, H. Irie, S. Hatakeyama (1998)
Concise enantioselective synthesis of (+)-aspicilin based on a ruthenium catalyzed olefin metathesis reactionTetrahedron Letters, 39
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R. Grigg, V. Sridharan, M. York (1998)
Sequential and cascade olefin metathesis — intramolecular Heck reactionTetrahedron Letters, 39
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P. Evans, V. Murthy (1998)
Temporary Silicon-Tethered Ring-Closing Metathesis Approach to C(2)-Symmetrical 1,4-Diols: Asymmetric Synthesis of D-Altritol.The Journal of organic chemistry, 63 20
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S. Hansen, Martin Volland, F. Rominger, Frank Eisenträger, P. Hofmann (1999)
Neuartige Ruthenium‐Carbenkomplexe: Synthese und Struktur hochaktiver Katalysatoren für die OlefinmetatheseAngewandte Chemie, 111
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G. Rapenne, and Dietrich-Buchecker, J. Sauvage (1999)
Copper(I)- or Iron(II)-Templated Synthesis of Molecular Knots Containing Two Tetrahedral or Octahedral Coordination SitesJournal of the American Chemical Society, 121
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High Molecular Weight Poly(p-phenyleneethynylene)s by Alkyne Metathesis Utilizing “Instant” Catalysts: A Synthetic StudyMacromolecules, 32
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J. Winkler, J. Stelmach, J. Axten (1996)
Two highly efficient syntheses of scalemic azocinesTetrahedron Letters, 37
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J. Clark, G. Trevitt, Dean Boyall, B. Stammen (1998)
Synthesis of alkenyl-substituted cyclic enol ethers by catalytic ring-closing metathesis of alkynyl ethersChemical Communications
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O. Sellier, P. Weghe, J. Eustache (1999)
Ring closing metathesis of sterically hindered 1,6 - dienes: A new approach to 5-membered branched cyclitolsTetrahedron Letters, 40
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J. Pernerstorfer, M. Schuster, S. Blechert* (1999)
A Solid-Phase Synthesis of Functionalized 6-, 7- and 8-Membered Azacycles via Olefin MetathesisSynthesis, 1999
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Matthias Schneider, S. Blechert (1996)
Synthese hochsubstituierter Cyclopentan‐ und Tetrahydrofuranderivate durch gekreuzte OlefinmetatheseAngewandte Chemie, 108
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C. Sturino, Jerome Wong (1998)
The ring-closing metathesis of vinyl ethers with Grubbs' catalyst for the synthesis of dihydropyransTetrahedron Letters, 39
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Michael Marsella, Heather Maynard, R. Grubbs (1997)
Templatgesteuerte Ringschlußmetathesen: Synthese und Polymerisation ungesättigter KronenetherAngewandte Chemie, 109
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K. Nicolaou, K. Nicolaou, N. Winssinger, N. Winssinger, Joaquin Pastor, Joaquin Pastor, S. Ninkovic, S. Ninkovic, Francisco Sarabia, Francisco Sarabia, Yun He, Yun He, D. Vourloumis, D. Vourloumis, Zhen Yang, Zhen Yang, Tianhu Li, P. Giannakakou, Ernest Hamel (1997)
Synthesis of epothilones A and B in solid and solution phaseNature, 387
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N. Pschirer, U. Bunz (1999)
Alkyne metathesis with simple catalyst systems: High yield dimerization of propynylated aromatics; scope and limitationsTetrahedron Letters, 40
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Hiroyuki Katayama, F. Ozawa (1998)
Convenient Routes to Vinylideneruthenium Dichlorides with Basic and Bulky Tertiary Phosphine Ligands (PPri3 and PCy3)Organometallics, 17
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Principles and applications of organotransition metal chemistry -
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Ruthenium Carbene-Based Olefin Metathesis Initiators: Catalyst Decomposition and LongevityJournal of Organic Chemistry, 64
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Synthesis and structural characterization of macrocyclic carbohydrate derivatives obtained from catalytic metathesis reaction with chloro-aryloxide complexes of tungstenTetrahedron, 52
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Conformationally Unbiased Macrocyclization Reactions by Ring Closing Metathesis.The Journal of organic chemistry, 61 12
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P. Wipf, W. Weiner (1999)
Enantioselective Synthesis and Photoracemization Studies of (+)-2-Cyclopropyl-7,8-dimethoxy-2H- chromene-5-carboxylic Acid Methyl Ester, an Advanced Intermediate of a Dihydrofolate Reductase Inhibitor.The Journal of organic chemistry, 64 14
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Titanocene(II)-Promoted Cyclization of Unsaturated ThioacetalsSynlett, 1999
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Total Synthesis of (−)‐Epothilone AAngewandte Chemie, 36
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W. Zuercher, M. Scholl, R. Grubbs (1998)
Ruthenium-Catalyzed Polycyclization ReactionsJournal of Organic Chemistry, 63
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A. Fürstner, K. Langemann (1996)
A Concise Total Synthesis of Dactylol via Ring Closing Metathesis.The Journal of organic chemistry, 61 25
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M. Delgado, Julio Martín (1997)
Ortho-Condensed oxane/polyoxygenated macrorings by ruthenium-catalyzed ring closing metathesisTetrahedron Letters, 38
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M. Scholl, Tina Trnka, John Morgan, R. Grubbs (1999)
Increased ring closing metathesis activity of ruthenium-based olefin metathesis catalysts coordinated with imidazolin-2-ylidene ligandsTetrahedron Letters, 40
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R. Roy, S. Das (2000)
Recent applications of olefin metathesis and relatedreactions in carbohydrate chemistryChemical Communications
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L. Ackermann, A. Fürstner, T. Weskamp, F. Kohl, W. Herrmann (1999)
Ruthenium Carbene Complexes with Imidazolin-2-ylidene Ligands Allow the Formation of Tetrasubstituted Cycloalkenes by RCMTetrahedron Letters, 40
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Ruthenium-catalysed ring-opening metathesis polymerization of cycloolefins initiated by diazoestersJournal of Molecular Catalysis, 76
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M. Schuster, S. Blechert* (1998)
RUTHENIUM-CATALYZED YNE-ENE CROSS METATHESIS IMMOBILIZATION OF FUNCTIONALIZED ALKYNESTetrahedron Letters, 39
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M. Crimmins, A. Choy (1997)
Asymmetric Aldol-Ring-Closing Metathesis Strategy for the Enantioselective Construction of Six- to Nine-Membered Oxygen Heterocycles.The Journal of organic chemistry, 62 22
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K. Weiss, A. Michel, Eva‐Maria Auth, Uwe Bunz, Timo Mangel, Klaus Müllen (1997)
Acyclische Diinmetathese (ADIMET), ein effizienter Weg zu hochmolekularen Poly(phenylen)ethinylenen (PPEs) und nichtkonjugierten Polyalkinylenen†‡Angewandte Chemie, 109
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M. Delgado, Julio Martín (1999)
Ring-Closing Metathesis in the Synthesis of Large and Medium-Sized Oxacycles. Application to the Synthesis of Polyoxygenated Macrocycles.The Journal of organic chemistry, 64 13
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A. Fürstner (1997)
Recent advancements in ring closing olefin metathesisTopics in Catalysis, 4
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D. Robson, V. Gibson, R. Davies, M. North (1999)
A New and Highly Efficient Grubbs Initiator for Ring-Opening Metathesis PolymerizationMacromolecules, 32
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S. Burke, K. Quinn, V. Chen (1998)
Synthesis of a C(22)−C(34) Halichondrin B Precursor via Ring Opening−Double Ring Closing MetathesisJournal of Organic Chemistry, 63
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A. Piscopio, John Miller, K. Koch (1999)
Ring closing metathesis in organic synthesis: Evolution of a high speed, solid phase method for the preparation of β-turn mimeticsTetrahedron, 55
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O. Dirat, C. Kouklovsky, Y. Langlois*, P. Lesot, J. Courtieu (1999)
Double diastereoselection in asymmetric [2+3] cycloaddition of chiral oxazoline N-oxides: application to the kinetic resolution of a racemic α,β-unsaturated δ-lactoneTetrahedron-asymmetry, 10
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Luisa Cabrejas, Stefan Rohrbach, D. Wagner, Jörg Kallen, G. Zenke, J. Wagner (1999)
Makrolidanaloga des neuartigen Immunsuppressivums Sanglifehrin: eine neue Anwendung der Ringschluß‐MetatheseAngewandte Chemie, 111
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R. Schrock, John Murdzek, G. Bazan, J. Robbins, M. DiMare, M. O'Regan (1990)
Synthesis of molybdenum imido alkylidene complexes and some reactions involving acyclic olefinsJournal of the American Chemical Society, 112
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J. Winkler, Joanne Holland, Jiri Kasparec, P. Axelsen (1999)
Design and synthesis of constrained epothilone analogs: The efficient synthesis of eleven-membered rings by olefin metathesisTetrahedron, 55
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M. Sasaki, Tetsuji Noguchi, K. Tachibana (1999)
Synthesis of the FGH ring fragment of ciguatoxinTetrahedron Letters, 40
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John Tallarico, Michele Randall, M. Snapper (1997)
Selectivity in ring-opening metathesesTetrahedron, 53
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M. Tori, K. Nakashima, R. Ito, M. Sono (2000)
Olefin Metathesis Reactions of Some Aromatic Dienes with ortho- and meta-Disubstitution.Formation of 10-,12-,14-,and 17-Membered Cyclic Compounds and Isomerization of an Allylic AlcoholHeterocycles, 53
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B. Schmidt, H. Wildemann (1999)
Synthesis of Functionalized 2,3- and 3,4-Dihydropyrans Starting from α-Hydroxycarboxylic Esters via RCMSynlett, 1999
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Jinkun Huang, E. Stevens, S. Nolan, J. Petersen (1999)
Olefin Metathesis-Active Ruthenium Complexes Bearing a Nucleophilic Carbene LigandJournal of the American Chemical Society, 121
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Sukbok Chang, L. Jones, Chunming Wang, L. Henling, R. Grubbs (1998)
Synthesis and Characterization of New Ruthenium-Based Olefin Metathesis Catalysts Coordinated with Bidentate Schiff-Base LigandsOrganometallics, 17
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P. Harrington, M. Tius (1999)
A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core.Organic letters, 1 4
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M. Snapper, and Tallarico, Michele Randall (1997)
Regio- and Stereoselective Ring-Opening Cross-Metathesis. Rapid Entry into Functionalized Bicyclo[6.3.0] Ring SystemsJournal of the American Chemical Society, 119
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M. Quitschalle, M. Kalesse (1999)
Improved synthesis of the northern hemisphere of epothilone A by a Sharpless asymmetric dihydroxylationTetrahedron Letters, 40
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J. Cossy, David Bauer, V. Bellosta (1999)
A short synthesis of the C1–C7 fragment of methymycin by ring-closing olefin metathesisTetrahedron Letters, 40
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M. Schuster, S. Blechert (1997)
Die Olefinmetathese in der organischen SyntheseAngewandte Chemie, 109
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W. Herrmann, Wolfgang Schattenmann, O. Nuyken, Stephan Glander (1996)
Allylruthenium(IV)‐Komplexe als hocheffiziente ROMP‐KatalysatorenAngewandte Chemie, 108
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Seongkon Kim, Israel Figueroa, P. Fuchs (1997)
APPLICATION OF THE GRUBBS RING-CLOSING METATHESIS FOR THE CONSTRUCTION OF A MACROCYCLIC ANSA-BRIDGE. SYNTHESIS OF THE TRICYCLIC CORE OF ROSEOPHILINTetrahedron Letters, 38
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A. Fürstner, T. Gastner, H. Weintritt (1999)
A Second Generation Synthesis of Roseophilin and Chromophore AnaloguesJournal of Organic Chemistry, 64
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M. Bujard, V. Gouverneur, C. Mioskowski (1999)
A Highly Efficient and Practical Synthesis of Cyclic Phosphinates Using Ring-Closing Metathesis.The Journal of organic chemistry, 64 6
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O. Dirat, Thierry Vidal, Y. Langlois* (1999)
A new route to C-glycosylidene compounds mediated by olefin metathesisTetrahedron Letters, 40
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Arnab Chatterjee, R. Grubbs (1999)
Synthesis of trisubstituted alkenes via olefin cross-metathesis.Organic letters, 1 11
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J. Clark, Olivier Hamelin, R. Hufton (1998)
Synthesis of medium-sized cyclic allylic ethers by ring-closing metathesis and subsequent elaboration to sub-units found in the brevetoxins and ciguatoxinsTetrahedron Letters, 39
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T. Belderrain, R. Grubbs (1997)
Reaction between Ruthenium(0) Complexes and Dihalo Compounds. A New Method for the Synthesis of Ruthenium Olefin Metathesis CatalystsOrganometallics, 16
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A. Barrett, S. Baugh, D. Braddock, K. Flack, V. Gibson, P. Procopiou (1997)
Enyne metathesis for the facile synthesis of highly functionalisednovel bicyclic β-lactamsChemical Communications
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Laleh Jafarpour, Jinkun Huang, E. Stevens, S. Nolan (1999)
(p-cymene)RuLCl2 (L = 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene and 1,3-Bis(2,6-diisopropylphenyl)imidazol-2-ylidene) and Related Complexes as Ring Closing Metathesis CatalystsOrganometallics, 18
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O. Arjona*, Aurelio Csáky, and Murcia, J. Plumet (1999)
Regioselective Ring-Opening and Cross-Coupling Metathesis of 2-Substituted 7-Oxanorbornenes. New Stereoselective Entry into Trisubstituted TetrahydrofuransJournal of Organic Chemistry, 64
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A. Fürstner, K. Langemann (1997)
Total Syntheses of (+)-Ricinelaidic Acid Lactone and of (−)-Gloeosporone Based on Transition-Metal-Catalyzed C−C Bond FormationsJournal of the American Chemical Society, 119
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Michele Randall, M. Snapper (1998)
Selective olefin metatheses—new tools for the organic chemist: A reviewJournal of Molecular Catalysis A-chemical, 133
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Selektive ringöffnende Olefinmetathese mit funktionalisierten monosubstituierten OlefinenAngewandte Chemie, 109
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Application of Ring-Closing Metathesis to the Synthesis of Rigidified Amino Acids and PeptidesJournal of the American Chemical Society, 118
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Tandem Ring Opening−Ring Closing Metathesis of Cyclic OlefinsJournal of the American Chemical Society, 118
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Convenient synthesis of novel macrocyclic urethanes: alkoxycarbonylation of amines and ring-closing metathesis strategy.Tetrahedron letters, 39 14
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Ring closing metathesis guided synthesis of (R)-(–)-musconeJournal of The Chemical Society-perkin Transactions 1
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Further Studies on Total Synthesis of Sarain A. Efforts Toward Annulation of the Macrocyclic RingsJournal of Organic Chemistry, 64
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„Rolling Loop Scan”︁: Aufbau von Bibliotheken aus Peptiden, die bioaktive Konformationen oder lokale Faltungen von Peptiden und Proteinen imitieren, durch RingschlußmetatheseAngewandte Chemie, 111
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Synthesis of macrocyclic lactams and lactones via ring-closing olefin metathesisTetrahedron Letters, 39
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Novel liquid-crystalline PPE-naphthalene copolymers displaying blue solid-state fluorescenceChemical Communications
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Mo[N(t-Bu)(Ar)]3 Complexes As Catalyst Precursors: In Situ Activation and Application to Metathesis Reactions of Alkynes and DiynesJournal of the American Chemical Society, 121
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- Publisher
- Wiley
- Copyright
- Copyright © 2000 Wiley Subscription Services
- ISSN
- 0044-8249
- eISSN
- 1521-3757
- DOI
- 10.1002/1521-3757(20000901)112:17<3140::AID-ANGE3140>3.0.CO;2-G
- Publisher site
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Abstract
Die Entwicklung definierter Katalysatoren für die Olefinmetathese, die sich durch hohe Aktivität, Stabilität und exzellente Toleranz gegenüber polaren funktionellen Gruppen auszeichnen, hat dieses Forschungsgebiet revolutioniert. Im Verlauf des letzten Jahrzehnts wurden diese neuartigen metallorganischen Reagentien rasch von der Organischen Chemie sowie der Polymerchemie vereinnahmt. Eine Fülle eleganter Anwendungen auf die Synthese von Naturstoffen und anderen Verbindungen bezeugt diese Erfolgsgeschichte. Dieser Aufsatz bietet einen Überblick über den Fortschritt in diesem Bereich und versucht, die jüngsten Entwicklungen zu skizzieren, die eine noch größere Anwendungsbreite der Reaktion in Aussicht stellen. Anhand ausgewählter Beispiele wird der nachhaltige Einfluss der Metathese auf die Logik der Syntheseplanung diskutiert. Auch wird gezeigt, dass die Metathese keinesfalls auf Alkene als Substrate beschränkt ist. Zuletzt wird auf bislang wenig beachtete Möglichkeiten eingegangen, wie Metathesereaktionen abseits der wohl etablierten mechanistischen Pfade durchführbar sind.
Journal
Angewandte Chemie – Wiley
Published: Jan 1, 2000
Keywords: ; ; ; ;