Grubbs / O'Leary Handbook of Metathesis

Applications in Organic Synthesis
2. vollständig überarbeitete und erweiterte Auflage 2015
ISBN: 978-3-527-69402-0
Verlag: Wiley-VCH
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 744 Seiten, E-Book

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

Autoren/Hrsg.

Grubbs, Robert H.

O'Leary, Daniel J.

Inhaltsverzeichnis

Preface

 

GENERAL RING-CLOSING METATHESIS

Introduction

Carbocycles (Introduction)

Synthesis of Bridged Bicycloalkenes

Synthesis of Heterocycles Containing Si, P, S, or B

Synthesis of O-Heterocycles

Synthesis of N-Heterocycles

Synthesis of Cyclic Conjugated Dienes

Alkyne Metathesis

Enyne Metathesis

Tandem Processes

Synthesis of Macrocycles

RCM and Isomerization via Ru-H

Relay RCM (RRCM)

Z-Selective RCM

Enantioselective RCM

Conclusion

 

CROSS-METATHESIS

Early Examples Using Well-Defined Molybdenum and Ruthenium Catalysts

The General Model for Selectivity in CM Reactions

Definition of Cross-Metathesis Reaction Categories and Chapter Organization

Hydrocarbons

Boron

Nitrogen

Oxygen

Halides

Phosphorus

Sulfur

Fragment Coupling Reactions

Conclusions

 

VIGNETTE: EXTENDING THE APPLICATION OF METATHESIS IN CHEMICAL BIOLOGY - THE DEVELOPMENT OF SITE-SELECTIVE PEPTIDE AND PROTEIN MODIFICATIONS

Introduction

Cross-Metathesis Methodology Studies in Aqueous Media

Strategies for Allyl Chalogenide Incorporation into Proteins

Olefin Metathesis on Proteins

Outlook

 

RUTHENIUM-CATALYZED TANDEM METATHESIS/NON-METATHESIS PROCESSES

Introduction

Metathesis/Isomerization

Metathesis/Hydrogenation

Metathesis/Oxidation

Metathesis/Cyclization

Metathesis/Atom-Transfer Radical Addition

Metathesis/Rearrangement

Metathesis/Cyclopropanation

Metathesis/Miscellaneous

Conclusions

 

ENYNE METATHESIS

Introduction

Enyne Metathesis

Strategic Application of Enyne Metathesis in Organic Synthesis

Perspective

 

ALKYNE METATHESIS

Introduction

Background Information

Molybdenum Alkylidyne Catalysts with Silanolate Ligands

Other Catalytically Active Molybdenum Alkylidyne Complexes

Novel Tungsten Alkylidyne Catalysts

Basic Types of Applications

Selected Applications

Conclusions

 

CATALYST-CONTROLLED STEREOSELECTIVE OLEFIN METATHESIS

Introduction

Enantioselective 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 Complexes

Z-Selective Olefin Metathesis Reactions with Ru Complexes

Z-Selective Ring-OpeningMetathesis Polymerization

Conclusions and Outlook

 

TWO VIGNETTES: RCM IN NATURAL PRODUCT TOTAL SYNTHESIS

Vignette 1: Allylsilane RCM/Electrophilic Desilylation as a Means to Access Rings with Exocyclic Alkenes

Vignette 2: Synthesis of Antimetastatic Agents Using Ring-Closing Metathesis

 

METATHESIS OF SILICON-CONTAINING OLEFINS

Introduction

Homo and Cross-Metathesis versus Silylative Coupling of Vinylsilicon Compounds

Homometathesis of Allylsilanes and Their Cross-Metathesis with Olefins

Silylative Coupling versus Cross-Metathesis of Vinylsilanes in Sequential Synthesis of Functionalized Alkenes

Silylative Coupling Cyclization of Silicon-Containing Dienes

Ring-Closing Metathesis of Silicon-Containing Dienes

Acyclic Diene Metathesis (ADMET) versus Silylative Coupling (SC) Polycondensation of Silicon-Containing Dienes

Ring-OpeningMetathesis Polymerization of Silyl-Substituted Cycloalkenes

 

RING-CLOSING METATHESIS IN THE LARGE-SCALE SYNTHESIS OF PHARMACEUTICALS

Introduction

Ciluprevir (BILN2061) and Analogs

Vaniprevir (MK-7009)

Simeprevir (TMC435)

SB-462795

Approaches to the Scale-Up of RCM Reactions

 

METATHESIS STRATEGIES IN DIVERSITY-ORIENTED SYNTHESIS

Introduction

Synthesis of Small- to Medium-Sized Rings via Metathesis Strategies

Synthesis of Macrocycles via Metathesis Strategies

Metathesis Cascade Strategies in Diversity-Oriented Synthesis

Synthesis of Small- to Medium-Sized Rings via Metathesis Cascade Strategies

Synthesis of Macrocycles via Metathesis Cascade Strategies

Metathesis Strategies in Solid-Phase Library Synthesis

Immobilized Scavengers and Catalysts

Conclusions

 

OLEFIN METATHESIS: COMMERCIAL APPLICATIONS AND FUTURE OPPORTUNITIES

Introduction

Ruthenium Olefin Metathesis Catalysts

Renewable Seed Oil Feedstocks

Production of Fatty Acids and Amino Acids from Renewables

Olefin Metathesis and Natural Materials Chemistry

Pha

Über Autor(innen)

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.