Asymmetric Organocatalysis

Asymmetric catalysis represents still one of the major challenges in modern organic chemistry. Besides the well-established asymmetric metal-complex-catalysed syntheses and biocatalysis, the use of "pure" organic catalysts turned out to be an additional efficient tool for the synthesis of chiral building blocks. In this handbook, the experienced authors from academia and industry provide the first overview of the important use of such metal-free organic catalysts in organic chemistry. With its comprehensive description of numerous reaction types, e.g., nucleophilic substitution and addition reactions as well as cycloadditions and redox reactions, this book targets organic chemists working in industry and academia, and deserves a place in every laboratory.Die enantioselektive Synthese ist eine eine Herausforderung für den modernen Organiker. Die weit verbreitete enantioselektive Katalyse mittels chiraler Metallkomplexe kann Probleme bei der Produktabtrennung verursachen. Eine elegante Alternative ist die Katalyse mittels kleiner chiraler organischer Moleküle. Das erfahrene Autorengespann aus Hochschule und Industrie gibt mit diesem Handbuch erstmals eine Übersicht über den Einsatz solcher nicht metallhaltiger Katalysatoren in der Laborpraxis.
Alle wichtigen Reaktionstypen wie nucleophile Substitution, nucleophile Addition, Cycloaddition, Oxidation und Reduktion werden behandelt. Daneben werden verschiedene Verfahren zur Racemattrennung vorgestellt. Ein zusätzlicher Fokus liegt auf den industriellen Anwendungsmöglichkeiten der neuen Verfahren.
Mit einer umfassenden Beschreibung der Synthesestrategien und Methoden wendet sich dieses Buch an den praktisch arbeitenden Chemiker in Industrie und Hochschule und sollte in keinem Labor fehlen. Introduction
General Mechanistic Considerations
Nucleophilic Substitution at Aliphatic Carbon
Nucleophilic Addition to Electron-deficient C=C Double Bonds
Nucleophilic Addition to C=N Double Bonds
Nucleophilic Addition to C=O Double Bonds
Nucleophilic Addition to Unsaturated Nitrogen
Cycloaddition Reactions
Protonation of Enolates and Tautomerization of Enols
Oxidation
Reduction of Carbonyl Compounds
Kinetic Resolution of Racemic Alcohols and Amines
Desymmetrization and Kinetic Resolution of Anhydrides
Large-Scale Applications
Appendix: Tabular Survey of Organo-Catalysts, Synthesis and Application Introduction
General Mechanistic Considerations
Nucleophilic Substitution at Aliphatic Carbon
Nucleophilic Addition to Electron-deficient C=C Double Bonds
Nucleophilic Addition to C=N Double Bonds
Nucleophilic Addition to C=O Double Bonds
Nucleophilic Addition to Unsaturated Nitrogen
Cycloaddition Reactions
Protonation of Enolates and Tautomerization of Enols
Oxidation
Reduction of Carbonyl Compounds
Kinetic Resolution of Racemic Alcohols and Amines
Desymmetrization and Kinetic Resolution of Anhydrides
Large-Scale Applications
Appendix: Tabular Survey of Organo-Catalysts, Synthesis and Application
"This fascinating monograph captures the diversity and power of an area of research whose roots extend deep within the organic chemistry literature, yet which has only recently achieved critical mass through the collective contributions of many present-day pioneers. ... is an essential addition to both academic and industrial research libraries, as well as to the personal collection of any scientist with an interest in catalysis or synthetic chemistry." Angewandte Chemie I.E.

"... well-written with clear, focused schemes... of great value to those involved in synthetic methodology, catalysis, and total synthesis." Journal of the American Chemical Society

"On the whole, the authors succeeded in covering a very broad range of reactions that are catalyzed by organic catalysts, and offer readers an excellent overview of the current situation in the field of asymmetric organocatalysis. This book can be recommended for all scientists working in the area of asymmetric catalysis, whether in industrial research and development or at the universities. Postgraduate students and postdoctoral researchers who have begun work on this rapidly growing field would derive considerable benefit from reading it."
Synthesis

"This monograph will be a valuable addition into personal collections of synthetic chemists and research libraries of academia and industry." E-STREAMS "Bas Buch von Berkessel und Gröger ist eine umfangreiche Monographie über die asymmetrische Organokatalyse. Obwohl es schwierig ist, ein Buch über ein sich so rasch entwickelndes Gebiet zu schreiben, ist es den Autoren gelungen, dieses auf aktuellen Stand zu bringen. ... Die Lektüre dieses Buches sollte Pflicht sein für alle, die sich mit Organokatalyse befassen. Darüber hinaus ist es all denjenigen zu empfehlen, die sich für asymmetrische Katalyse oder organische Synthese interessieren. Das Buch gehört in jede chemische Bibliothek, und sollte in die Lehre der modernen Methoden der organischen Chemie Eingang finden."

Maria Hechavarria Fonseca, Mülheim/Ruhr, Nachrichten aus der Chemie, 05/2005


"...wird Generationen von Chemikern als Einführung in die moderne asymmetrische Organokatalyse dienen: Es ist das Buch schlechthin zum Thema."
Christian Burstein, Frank Glorius, Philipps-Universität Marburg
Angewandte Chemie + International Edition 2005 - 117/28




Albrecht Berkessel is full professor at the university of Cologne, Germany. His research interests are catalysis, combinatorial chemistry and solid phase chemistry.
Harald Groger is currently working at the Degussa AG. His research is focussed on enzymatic reactions and biocatalysis. Asymmetric catalysis is of ever-increasing importance in organic synthesis, both in the academic and the industrial environment. Between the extremes of metal-based and biocatalytic methods, the use of low-molecular weight and purely organic catalysts has become a third and highly efficient tool for enantioselective transformations. In this book, two experienced authors from academia and industry provide the first comprehensive overview of both the development and the current state of asymmetric organocatalysis. After a historical introduction, all synthetically relevant reaction types, such as nucleophilic substitution, addition to C=X bonds, cycloadditions and redox reactions are thoroughly discussed in a total of 11 chapters, followed by a consideration of large scale applications of organocatalysis. Additionally, the most frequently used organocatalysts and their properties are summarized in an appendix, aiding the research chemist in selecting an appropriate catalyst for a given transformation. Overall, this book targets organic chemists active both in industry and academia, and it deserves a place in every laboratory.


From the Contents:

- Introduction: Organocatalysis - From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis
- Nucleophilic Substitution at Aliphatic Carbon, e.g. Amino Acid Synthesis by Alkylation
- Nucleophilic Addition to C=C, C=N, C=O, N=N and N=O Double Bonds
- Synthesis of Epoxides and Aziridines
- Cycloaddition Reactions
- Protonation of Enolates
- Oxidation/Reduction
- Kinetic Resolution of Racemic Alcohols and Amines
- Desymmetrization of meso- and prochiral Compounds
- Large-scale Applications
- Appendix: Tabular Survey of Frequently used Organocatalysts