Asymmetric Organocatalysis

Asymmetric synthesis is a challenge for the modernday organic chemist. The widely used asymmetric catalysis using chiral metal complexes often causes problems in dividing the products. The use of potentially toxic metal catalysts is particularly unwelcome in the synthesis of pharmaceutical substances and reactants in biomedical analysis.

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.

Autorentext
Albrecht Berkessel is full professor at the university of Cologne, Germany. His research interests are catalysis, combinatorial chemistry and solid phase chemistry. Harald Gröger is currently working at the Degussa AG. His research is focussed on enzymatic reactions and biocatalysis.

Klappentext
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

Inhalt
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

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