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The second edition of the "go-to" reference in this field is completely updated and features more than 80% new content, with emphasis on new developments in the field, especially in industrial applications. No other book covers the topic in such a comprehensive manner and in such high quality. Edited by the Nobel laureate R. H. Grubbs and D. J. O´Leary, this volume 2 of the 3-volume work focusses on applications in organic synthesis. With a list of contributors that reads like a "Who's-Who" of metathesis, this is an indispensable one-stop reference for chemists in academia and industry.Other available volumes:Volume 1: Catalyst Development and Mechanism, Editors: R. H. Grubbs and A. G. WenzelVolume 3: Polymer Synthesis, Editors: R. H. Grubbs and E. Khosravi
Sommario
PrefaceGENERAL RING-CLOSING METATHESISIntroductionCarbocycles (Introduction)Synthesis of Bridged BicycloalkenesSynthesis of Heterocycles Containing Si, P, S, or BSynthesis of O-HeterocyclesSynthesis of N-HeterocyclesSynthesis of Cyclic Conjugated DienesAlkyne MetathesisEnyne MetathesisTandem ProcessesSynthesis of MacrocyclesRCM and Isomerization via Ru-HRelay RCM (RRCM)Z-Selective RCMEnantioselective RCMConclusionCROSS-METATHESISEarly Examples Using Well-Defined Molybdenum and Ruthenium CatalystsThe General Model for Selectivity in CM ReactionsDefinition of Cross-Metathesis Reaction Categories and Chapter OrganizationHydrocarbonsBoronNitrogenOxygenHalidesPhosphorusSulfurFragment Coupling ReactionsConclusionsVIGNETTE: EXTENDING THE APPLICATION OF METATHESIS IN CHEMICAL BIOLOGY - THE DEVELOPMENT OF SITE-SELECTIVE PEPTIDE AND PROTEIN MODIFICATIONSIntroductionCross-Metathesis Methodology Studies in Aqueous MediaStrategies for Allyl Chalogenide Incorporation into ProteinsOlefin Metathesis on ProteinsOutlookRUTHENIUM-CATALYZED TANDEM METATHESIS/NON-METATHESIS PROCESSESIntroductionMetathesis/IsomerizationMetathesis/HydrogenationMetathesis/OxidationMetathesis/CyclizationMetathesis/Atom-Transfer Radical AdditionMetathesis/RearrangementMetathesis/CyclopropanationMetathesis/MiscellaneousConclusionsENYNE METATHESISIntroductionEnyne MetathesisStrategic Application of Enyne Metathesis in Organic SynthesisPerspectiveALKYNE METATHESISIntroductionBackground InformationMolybdenum Alkylidyne Catalysts with Silanolate LigandsOther Catalytically Active Molybdenum Alkylidyne ComplexesNovel Tungsten Alkylidyne CatalystsBasic Types of ApplicationsSelected ApplicationsConclusionsCATALYST-CONTROLLED STEREOSELECTIVE OLEFIN METATHESISIntroductionEnantioselective Ring-Opening/Cross-Metathesis (EROCM)Enantioselective Ring-Opening/Ring-Closing Metathesis (ERORCM)Enantioselective Ring-Closing Metathesis (ERCM)Z-Selective Olefin Metathesis Reactions with Mo- andW-Based ComplexesZ-Selective Olefin Metathesis Reactions with Ru ComplexesZ-Selective Ring-OpeningMetathesis PolymerizationConclusions and OutlookTWO VIGNETTES: RCM IN NATURAL PRODUCT TOTAL SYNTHESISVignette 1: Allylsilane RCM/Electrophilic Desilylation as a Means to Access Rings with Exocyclic AlkenesVignette 2: Synthesis of Antimetastatic Agents Using Ring-Closing MetathesisMETATHESIS OF SILICON-CONTAINING OLEFINSIntroductionHomo and Cross-Metathesis versus Silylative Coupling of Vinylsilicon CompoundsHomometathesis of Allylsilanes and Their Cross-Metathesis with OlefinsSilylative Coupling versus Cross-Metathesis of Vinylsilanes in Sequential Synthesis of Functionalized AlkenesSilylative Coupling Cyclization of Silicon-Containing DienesRing-Closing Metathesis of Silicon-Containing DienesAcyclic Diene Metathesis (ADMET) versus Silylative Coupling (SC) Polycondensation of Silicon-Containing DienesRing-OpeningMetathesis Polymerization of Silyl-Substituted CycloalkenesRING-CLOSING METATHESIS IN THE LARGE-SCALE SYNTHESIS OF PHARMACEUTICALSIntroductionCiluprevir (BILN2061) and AnalogsVaniprevir (MK-7009)Simeprevir (TMC435)SB-462795Approaches to the Scale-Up of RCM ReactionsMETATHESIS STRATEGIES IN DIVERSITY-ORIENTED SYNTHESISIntroductionSynthesis of Small- to Medium-Sized Rings via Metathesis StrategiesSynthesis of Macrocycles via Metathesis StrategiesMetathesis Cascade Strategies in Diversity-Oriented SynthesisSynthesis of Small- to Medium-Sized Rings via Metathesis Cascade StrategiesSynthesis of Macrocycles via Metathesis Cascade StrategiesMetathesis Strategies in Solid-Phase Library SynthesisImmobilized Scavengers and CatalystsConclusionsOLEFIN METATHESIS: COMMERCIAL APPLICATIONS AND FUTURE OPPORTUNITIESIntroductionRuthenium Olefin Metathesis CatalystsRenewable Seed Oil FeedstocksProduction of Fatty Acids and Amino Acids from RenewablesOlefin Metathesis and Natural Materials ChemistryPharmaceutical ApplicationsROMP-Derived Oligomers for Facilitated SynthesisConclusionIndex
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Robert H. Grubbs received his Ph.D. from Columbia University for work with Ron Breslow. After a postdoctoral year with Jim Collman at Stanford University, he joined the faculty at Michigan State University. In 1978, he moved to the California Institute of Technology, where he is now the Victor and Elizabeth Atkins Professor of Chemistry. Among many other awards he received the Nobel Prize in 2005 for his research on the metathesis reaction. His research interests include polymer chemistry, organometallic catalysis, and development of new synthetic organic methodology.
Daniel J. O?Leary received his PhD at UCLA in the group of Prof. Frank A. L. Anet. Following an NSF postdoctoral fellowship with Prof. Yoshito Kishi at Harvard University, he became Assistant Professor at Pomona College, where he is presently the Carnegie Professor of Chemistry. His research interests are in the area of organic synthesis, isotope effects, and nuclear magnetic resonance.
Riassunto
The second edition of the "go-to" reference in this field is completely updated and features more than 80% new content, with emphasis on new developments in the field, especially in industrial applications. No other book covers the topic in such a comprehensive manner and in such high quality.
Edited by the Nobel laureate R. H. Grubbs and D. J. O´Leary, this volume 2 of the 3-volume work focusses on applications in organic synthesis. With a list of contributors that reads like a "Who's-Who" of metathesis, this is an indispensable one-stop reference for chemists in academia and industry.
Other available volumes:
Volume 1: Catalyst Development and Mechanism, Editors: R. H. Grubbs and A. G. Wenzel
Volume 3: Polymer Synthesis, Editors: R. H. Grubbs and E. Khosravi
