Enantioselective Organocatalysis: Catalysts, Reactions and Applications

Updated reference on the field of organocatalysis explaining the many advances made in the past 10 years Enantioselective Organocatalysis III presents easily accessible, summarized information on organocatalysis, from computational aspects to non-conventional strategies, with complete coverage of the main advances in the field in the past 10 years. The book is the continuation of Comprehensive Enantioselective Organocatalysis, retaining the main features of its predecessor but with a larger number of concise chapters. Experimental procedures are not presented in this edition as most of them are similar to those already discussed in the previous edition. Edited by a highly qualified researcher and contributed to by experts in the field, Enantioselective Organocatalysis III includes information on: Aminocatalysis-3 selected examples of aminocatalytic direct alpha-heteroatom functionalization and direct alpha-alkylation Organocatalytic dynamic kinetic resolution and organocatalysis in carbohydrate synthesis and polymer science Light-controlled organocatalysis by bifunctional single-catalyst systems and dual photo/organocatalytic strategies in asymmetric synthesis Strategies towards asymmetric organocatalysis at parts-per-million loadings and emerging organocatalyst classes from renewable sources Activation modes in asymmetric anion-binding catalysis and transformations with chiral phase-transfer catalysts Appealing to a broad readership, Enantioselective Organocatalysis III is an essential reference for chemists and other researchers seeking to stay on top this rapidly developing field.

Table of Contents:
1. AMINOCATALYSIS 1.1 Explaining Anomalies in Enamine Catalysis: "Downstream Species" as a New Paradigm for Stereocontrol 1.2 Synergistic Strategies in Aminocatalysis 1.3 New trends in amino Acid-derived and Peptides Organocatalysts 1.4 Recent advances in amine catalyzed organocatalytic transformations 2. ENANTIOSELECTIVE CARBONYL CATALYSIS ENABLED BY CHIRAL ALDEHYDES 3. HYDROGEN-BOND DONOR CATALYSIS 3.1 Non-Classical C-H center dot center dot center dot X Hydrogen Bonding and Its Role in Asymmetric Organocatalysis 3.2 Chiral guanidines and thiourea derivatives in asymmetric synthesis 3.3 Squaramide-Catalyzed Asymmetric Reactions 3.4 Recent advances in asymmetric reactions catalyzed by chiral phosphoric acids 3.5 Dual Bronsted-acid Organocatalysis: Cooperative Asymmetric Catalysis with Combined Phosphoric and Carboxylic Acids 3.6 Brønsted acid catalysts and ?silylium? Lewis acid precatalysts Imidodiphosphorimidates (IDPis) 3.7 Stronger Bronsted Acids: Recent Progress (Akiyama, T and Mori, K) 4. PHOSPHINE ORGANOCATALYSIS 5. ION-PAIRING CATALYSIS 5.1 Activation Modes in Asymmetric Anion-Binding Catalysis 5.2 Asymmetric counteranion-directed catalysis (ACDC) 5.3 Phosphonium Salts in Asymmetric Catalysis: A Journey in a Decade's Extensive Research Work 5.4 Recent Progress in Asymmetric Ion-Pairing Catalysis with Ammonium Salts 6. PHASE-TRANSFER CATALYSTS 6.1 Design of high-performance chiral phase-transfer catalysts with privileged structures 6.2 Assisted by Hydrogen-Bond Donors: Cinchona Quaternary Salts as Privileged Chiral Catalysts for Phase-Transfer Reactions 6.3 Phase-Transfer and Ion-Pairing Catalysis of Pentanidiums and Bisguanidiniums 7. HALOGEN, CHALCOGEN 7.1 Halogen, Chalcogen, Anion-pi Bonding and sigma-Hole Interactions in Catalysis 7.2 Halogen Bonding in Organic Synthesis and Organocatalysis 7.3 Chalcogen Bonding: An Overview 8. SULFUR YLIDES 9. CHIRAL HYPERVALENT IODINES: ACTIVE PLAYERS IN ASYMMETRIC SYNTHESIS 10. LEWIS BASE CATALYSIS PROMOTED NUCLEOPHILIC SUBSTITUTIONS - RECENT ADVANCES AND FUTURE DIRECTIONS 11. ACTIVATING PRONUCLEOPHILES WITH HIGH PK(A) VALUES: CHIRAL ORGANO-SUPERBASES 12. RECENT ADVANCES IN THE CHEMISTRY AND APPLICATIONS OF N-HETEROCYCLIC CARBENES 13. ENANTIOSELECTIVE REDOX AND RADICAL REACTIONS IN THE DARK BY CHIRAL CATALYSTS 14. ORGANOCATALYSIS IN INERT C-H BOND FUNCTIONALIZATION 15. ENANTIOSELECTIVE DESYMMETRIZATION REACTIONS IN ASYMMETRIC CATALYSIS 16. TWO AND MORE CATALYSTS SYSTEMS 16.1 Two and Multi-organocatalyst Systems 16.2 Combined Power of Organo- and Transition Metal Catalysis in Organic Synthesis 16.3 Asymmetric Reactions Enabled by Cooperative Enantioselective Amino- and Lewis Acid Catalysis 16.4 Organocatalysis and Biocatalysis Hand in Hand: Combining Catalysts in One-Pot Procedures 17. RECENT PROGRESS IN ORGANOCATALYTIC ASYMMETRIC DOMINO TRANSFORMATIONS 18. MULTICOMPONENT AND MULTICATALYTIC REACTIONS - A SYNTHETIC STRATEGY INSPIRED BY NATURE 19. STEREODIVERGENT ASYMMETRIC SYNTHESIS VIA ORGANOCATALYSIS 20. CATALYSTS RECOVERY STRATEGIES 20.1 Fluorous organocatalysis 20.2 Covalently Supported Ionic Liquid Phases: An Advanced Class of Recyclable Catalytic Systems 20.3 Polymer Supported organocatalysts 21. SUPRAMOLECULAR CATALYSIS 21.1 Harnessing DNA as a Designable Scaffold for Asymmetric Catalysis: Recent Advances and Future Perspectives 21.2 Chitosan Based Catalyst and Their Mode of Action 21.3 Functionalized Macrocycles in Supramolecular Organocatalysis 21.4 Nanopores of a Covalent Organic Framework: A Customizable Vessel for Organocatalysis 21.5 Asymmetric Catalysis Under 1D/2D Nanostructured Materials 21.6 Synthesis of Chiral Polymer Catalysts and Their Application to Asymmetric Reactions 21.7 Stable, crystalline, porous, covalent organic frameworks as a platform for chiral organocatalysts 21.7 Enabling protein-hosted organocatalytic transformations 22. SITE SELECTIVE AND REMOTE FUNCTIONALIZATION 22.1 Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts 22.2 N-Heterocyclic Carbene Catalysis via Azolium Dienolates: An Efficient Strategy for Remote Enantioselective Functionalizations 22.3 Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers 22.4 Site-selective reactions mediated by molecular containers 23. NON-CONVENTIONAL ACTIVATION METHODS 23.1 Mechanochemical Organocatalysis: Do High Enantioselectivities Contradict What We Might Expect? 23.2 Microwave-assisted Organo-catalyzed C-C and C-X (Heteroatom) Bond-forming Reactions 23.3 Modern Electrochemical Aspects for the Synthesis of Value-Added Organic Products 24. ORGANOCATALYSIS IN NON-CONVENTIONNAL MEDIAS 24.1 Organocatalysis in aqueous media 24.2 Chiral Ionic Liquids and Deep Eutectic Solvents in Asymmetric Synthesis 24.3 Application of Biobased Solvents in Asymmetric Catalysis 25. LIGHT IN ORGANOCATALYSIS 25.1 Recent Trends in Photocatalytic Enantioselective Reactions 25.2 Organophotoredox catalysis : reactions and Structure-Property Relationships of catalysts 25.3 Photoredox Dual Catalysis 26. SWITCHABLE CATALYSTS : DYNAMIC RESPONSIVE SYSTEMS FOR CATALYTIC FUNCTION 27. EMERGING SYSTEMS 27.1 Bio-Inspired Quinone Catalysis 27.2 Taurine: A Water Friendly Organocatalyst in Organic Reactions 27.3 Vitamin B1: A Versatile Organocatalyst for Organic Synthesis 27.4 Growing Impact of Carbohydrate-Based Organocatalysts 28. COMPUTATIONAL INSIGHTS 28.1 The Central Role of Nonbonding Interactions in Modern Covalent Organocatalysis 28.2 Transition State Models for Understanding the Origin of Chiral Induction in Asymmetric Catalysis 28.3 Catalyst Design Within Asymmetric Organocatalysis 29. APPLIED ORGANOCATALYSIS 29.1 Low-loading asymmetric organocatalysis 29.2 Asymmetric organocatalysis: an enabling technology for medicinal chemistry 29.3 New chemical processes to streamline carbohydrate synthesis 29.4 Organocatalytic Asymmetric Methodologies towards the Synthesis of Atropisomeric N-Heterocycles 29.5 Catalytic Enantioselective Construction of Spiro Quaternary Carbon Stereocenters 29.6 Organocatalyzed Asymmetric Synthesis of Axially, Planar, and Helical Chiral Compounds 29.7 Recent Advances in Organocatalytic Kinetic Resolution for the Synthesis of Functionalized Products 29.8 Recent applications of asymmetric organocatalytic annulation reactions in natural product synthesis 29.9 Green chemistry meets medicinal chemistry: a perspective on modern metal-free late-stage functionalization reactions 29.10 Synthesis of Cyclic Fragrances 29.11 Organocatalytic Atroposelective Synthesis of N-N Axially Chiral Indoles and Pyrroles by De Novo Ring Formation 29.12 Macromolecular architectures through organocatalysis 29.13 Flow Chemistry: Recent Developments in the Synthesis of Pharmaceutical Products 29.14 Asymmetric Organocatalytic Tandem/Domino Reactions to Access Bioactive Products 29.15 Synthesis of radio isotope labelled products with organocatalysis 30. VALORIZATION OF WASTE: SUSTAINABLE ORGANOCATALYSTS FROM RENEWABLE RESOURCES 31. HIGHLIGHTS OF THE RECENT PATENT LITERATURE: FOCUS ON ASYMMETRIC ORGANOCATALYSIS

About the Author :
Peter I. Dalko completed his graduate studies at the Technical University of Budapest (BME) and earned his PhD at Paris XI, France. He currently works at the Paris Cité University, France, (CNRS). His group focuses on the development of enantiocatalytic reactions for organic synthesis, the design and application of light-sensitive molecular probes allowing accurate four-dimensional control of biological events in complex tissues, and on the preparation of remotely controllable drug delivery systems with imaging ability.