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Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, 3 Volume Set

Peter I. Dalko (Editor)
ISBN: 978-3-527-33236-6
1638 pages
December 2013
Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, 3 Volume Set (3527332367) cover image
A much-needed overview reflecting the developments over the past five years, this is the most comprehensive handbook on organocatalysis. As such, all relevant catalyst systems are discussed in detail, as well as key strategies, reaction types, and important applications in total synthesis. The first two volumes cover catalyst structures and fundamental activation types. These chapters allow readers to familiarize themselves with the relatively complex interactions that make organocatalytic reactions selective; to gain an insight into the most efficient catalyst types; and to understand the importance of physical parameters that influence reactivity and selectivity. Volume three is structured around reaction types, i.e. nucleophile additions to C=X and C=C bonds; Friedel-Crafts reactions, organocatalytic sigmatropic reactions, regioselective reactions and desymmetrization strategies, ring-forming reactions, multicomponent (domino) reactions, multicatalyst systems and the application of organocatalytic reactions in multistep synthesis are discussed. An appendix recollecting catalyst structures with the adequate cross-references to the corresponding chapters rounds off the book.
With its contributions written by pioneers of the organocatalysis field, this book provides non-specialists with an introduction to the topic as well as serving as a valuable source for researchers in academia and industry searching for an up-to-date and comprehensive overview of this promising area of synthetic organic chemistry.
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PART I:  Amino Acid-derived Catalysts
Proline-Related Secondary Amine Catalysts and Applications
TMS-Prolinol Catalyst in Organocatalysis
Non-Proline Amino Acid Catalysts
Chiral Imidazolidinone (MacMillan's) Catalyst
Oligopeptides as Modular Organocatalytic Scaffolds
PART II. Non Amino Acid-derived Catalysts
Cinchonas and Cupreidines
Chiral C2 Catalysts
Planar Chiral Catalysts
Dynamic Approaches towards Catalyst Discovery
Part III: Appendix / Catalysts
PART I: Asymmetric Catalysis with Non-Covalent Interactions
Brønsted Acids
Brønsted Acids: Chiral Phosphoric Acid Catalysts in Asymmetric Synthesis
Brønsted Acids: Chiral (Thio)urea Derivatives
Brønsted Bases
Chiral Onium Salts (Phase-Transfer Reactions)
Lewis Acids
Lewis Bases
PART II: Asymmetric Catalysis with Covalent Interactions
Rationalizing Reactivity and Selectivity in Aminocatalytic Reactions
Carbene Catalysts
Oxides and Epoxides
PART III: Tuning Catalyst Activity and Selectivity by the Reaction Medium and Conditions
 "Non-Classical" Activation of Organocatalytic Reactions (Pressure, Microwave Irradiation..)
Ionic Liquid Organocatalysts
Polymer and Mesoporous Material Supported Organocatalysts
Water in Organocatalytic Reactions

PART I. Alpha-alkylation and Heteroatom Functionalization
SN2-Type Alpha-Alkylation and Allylation Reactions
Alpha-Alkylation by SN1-Type Reactions
Alpha-Heteroatom Functionalization of Carbonyl Compounds
PART II. Nucleophile Addition to C = X Bonds
Aldol and Mannich-Type Reactions
Hydrocyanation and Strecker Reactions
The Morita-Baylis-Hillman (MBH) and Hetero-MBH Reactions
Reduction of C=O and C=N
PART III: Nucleophile Addition to C = C Bonds
Addition to a,ß-Unsaturated Aldehydes and Ketones
Addition to Nitro-Olefins and Vinyl-Sulfones
Organocatalyzed Asymmetric Arylation and Heteroarylation Reactions
PART IV: Ring-Forming Reactions
Intramolecular Reactions
Formation of 3-, 4- and 5-Membered Cycles by Intermolecular Reactions
Diels-Alder and Hetero-Diels-Alder Reactions
PART V:  Increasing Complexity
Organocatalytic Radical and Electron Transfer Reactions
Organocatalytic Sigmatropic Reactions
Regio- and Position Selective Reactions and Desymmetrizations
Three or More Components Reactions (Single Catalyst Systems)
Multi-Catalyst Systems

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Peter I. Dalko studied chemistry at the Budapest Technical University (Hungary) and graduated from Paris XI University (France) under the supervision of Stephan D. Géro. After undertaking postdoctoral research with Sir Derek H. Barton at Texas A&M University (USA) and Yoshito Kishi at Harvard University he joined Janine Cossy's research group at the ESPCI in Paris. He is now a Research Director at the French Scientific Research Council (CNRS) at the Medical Faculty of Paris Descartes University. His research is focused on total synthesis of structurally complex natural products, development of organocatalytic reactions for synthesis and developing micro- and nanoscale technologies for biomedical researches.
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