Handbook of metathesis . Volume 2 Applications in organic synthesis / / editors, Prof. Robert H. Grubbs, Prof. Daniel J. O'Leary

• Record Nr.: UNINA9910828172403321
• Pubbl/distr/stampa: Weinheim an der Bergstrasse, Germany : , : Wiley-VCH, , 2015; ©2015
• ISBN: 3-527-69404-8; 3-527-69402-1
• Edizione: [2nd ed.]
• Descrizione fisica: 1 online resource (772 p.)
• Disciplina: 660.299
• Soggetti: Metathesis (Chemistry); Alkenes; Organic compounds - Synthesis
• Lingua di pubblicazione: Inglese
• Formato: Materiale a stampa
• Livello bibliografico: Monografia
• Note generali: Description based upon print version of record.
• Nota di bibliografia: Includes bibliographical references at the end of each chapters and index.
• Nota di contenuto: Cover; Contents; Preface; List of Contributors; List of Abbreviations; Chapter 1 General Ring-Closing Metathesis; 1.1 Introduction; 1.2 Carbocycles (Introduction); 1.2.1 Small-Sized Carbocycles; 1.2.2 Medium-Sized Carbocycles; 1.2.3 Spiro Carbocycles; 1.3 Synthesis of Bridged Bicycloalkenes; 1.4 Synthesis of Heterocycles Containing Si, P, S, or B; 1.4.1 Si-Heterocycles; 1.4.2 P-Heterocycles; 1.4.3 S-Heterocycles; 1.4.4 B-Heterocycles; 1.5 Synthesis of O-Heterocycles; 1.5.1 Small and Medium-Size Cyclic Ethers; 1.5.2 Polycyclic Ethers; 1.6 Synthesis of N-Heterocycles; 1.6.1 N-Heterocycles; 1.6.2 Small and Medium-Sized Lactams1.7 Synthesis of Cyclic Conjugated Dienes; 1.8 Alkyne Metathesis; 1.9 Enyne Metathesis; 1.9.1 General Enyne Metathesis; 1.9.2 Dienyne Metathesis; 1.10 Tandem Processes; 1.10.1 Tandem ROM/RCM; 1.10.2 Other Tandem RCMs; 1.11 Synthesis of Macrocycles; 1.11.1 Macrocycles; 1.11.2 Macrolactones; 1.11.3 Macrolactams; 1.12 RCM and Isomerization via Ru-H; 1.13 Relay RCM (RRCM); 1.14 Z-Selective RCM; 1.14.1 Substrate-Controlled Z-Selective RCM; 1.14.2 Catalyst-Controlled Z-Selective RCM; 1.15 Enantioselective RCM; 1.16 Conclusion; Acknowledgments; References; Chapter 2 Cross-Metathesis2.1 Early Examples Using Well-Defined Molybdenum and Ruthenium Catalysts; 2.2 The General Model for Selectivity in CM Reactions; 2.3 Definition of Cross-Metathesis Reaction Categories and Chapter Organization; 2.4 Hydrocarbons; 2.4.1 Alkane Extensions; 2.4.2 Unsaturated Hydrocarbons, Including Styrene; 2.4.3 Ethylene Cross-Metathesis; 2.5 Boron; 2.6 Nitrogen; 2.6.1 Amines; 2.6.2 Amines as CM Partners in Heterocycle Syntheses; 2.6.3 Acrylonitrile and Other Nitrile-Based CM Applications; 2.6.4 Other Nitrogenous Substrates; 2.7 Oxygen; 2.7.1 Primary Allylic Alcohols and Derivatives2.7.2 Secondary Allylic Alcohols and Derivatives; 2.7.3 Tertiary Allylic Alcohols and Derivatives; 2.7.4 Homoallylic Alcohols and Derivatives; 2.7.5 Vinyl Ethers; 2.7.6 Acrolein, Crotonaldehyde, and Methacrolein; 2.7.7 Methyl Vinyl Ketone and Related Systems; 2.7.8 Acrylic Acid; 2.7.9 Acrylic Acid Derivatives, Including Esters, Thioesters, and Amides; 2.8 Halides; 2.9 Phosphorus; 2.10 Sulfur; 2.11 Fragment Coupling Reactions; 2.11.1 Acetogenins; 2.11.2 Cross-Metathesis Selectivity; 2.11.3 Tuning Metathesis Selectivity; 2.11.4 CM as an Alternative Coupling Strategy2.11.5 CM-Based Analog Synthesis; 2.11.6 Polyene Metathesis; 2.11.7 Cross-Metathesis Reaction Optimization: Pinnaic Acid; 2.12 Conclusions; References; Chapter 3 Vignette: Extending the Application of Metathesis in Chemical Biology - The Development of Site-Selective Peptide and Protein Modifications; 3.1 Introduction; 3.2 Cross-Metathesis Methodology Studies in Aqueous Media; 3.2.1 Allyl Sulfides are Reactive Substrates in Olefin Metathesis; 3.2.2 Sulfur-Relayed Cross-Metathesis; 3.2.3 Application of Aqueous Metathesis of Allyl Sulfides in Synthesis
• Sommario/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.