Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis

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


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

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.

"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