ean 9783527324163 temática QUÍMICA GENERAL año Publicación 2009 idioma INGLÉS editorial WILEY formato CARTONÉ 157,30 €    PEDIR   NOVEDAD

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química general

This comprehensive review of cinchona-based chiralilty inducers and their applications covers every topic, including ligands, immobilization and organocatalysis. Each chapter summarizes the scope and limitations of the new methods and technologies, while the final chapter contains carefully selected working procedures of cinchona alkaloid-promoted reactions organized according to reaction type. Invaluable reading for anyone wanting to learn about the current state of this hot topic.

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AN OVERVIEW OF CINCHONA ALKALOIDS IN CHEMISTRY Brief History Active Sites in Cinchona Alkaloids and Their Derivatives Structural Information on Cinchona Alkaloids How This Book is Organized PART I: Cinchona Alkaloid Derivatives as Chirality Inducers in Metal-Catalyzed Reactions CINCHONA ALKALOIDS AS CHIRALITY TRANSMITTERS IN METAL-CATALYZED ASYMMETRIC REDUCTIONS Introduction Homogeneous Systems for Ketone Reductions Heterogeneous Pt and Pd Catalysts Modified with Cinchona Alkaloids Industrial Applications Conclusions CINCHONA ALKALOIDS AS CHIRAL LIGANDS IN ASYMMETRIC OXIDATIONS Introduction Asymmetric Dihydroxylation of Alkenes Aminohydroxylation Sulfur Oxidations Summary CINCHONA ALKALOIDS AND THEIR DERIVATIVES AS CHIRALITY INDUCERS IN METAL-PROMOTED ENANTIOSELECTIVE CARBON-CARBON AND CARBON-HETEROATOM BOND FORMING REACTIONS Introduction Nucleophilic Addition to Carbonyl or Imine Compounds Miscellaneous Reactions Cinchona-Based Chiral Ligands in C-F Bond Forming Reactions Conclusions PART II: Cinchona Alkaloid Derivatives as Chiral Organocatalysts CINCHONA-BASED ORGANOCATALYSTS FOR ASYMMETRIC OXIDATIONS AND REDUCTIONS Introduction Cinchona-Based Organocatalysts in Asymmetric Oxidations Cinchona-Based Organocatalysts in Asymmetric Reductions Conclusions CINCHONA-CATALYZED NUCLEOPHILIC ALPHA-SUBSTITUTION OF CARBONYL DERIVATIVES Introduction Organocatalytic Nucleophilic Alpha-Substitution of Carbonyl Derivatives Cinchona Alkaloids in Asymmetric Organocatalysis The Pioneer Works for Phase-Transfer Catalytic Alpha-Substitution Alpha-Substitution of Alpha-Amino Acid Derivatives via PTC Alpha-Substitution of Other Carbonyl Derivatives via PTC Alpha-Heteroatom Substitution via PTC Nucleophilic Alpha-Substitution of Carbonyl Derivatives via Non-PTC Conclusions CINCHONA-MEDIATED ENANTIOSELECTIVE PROTONATIONS Introduction Preformed Enolates and Equivalents Nucleophilic Addition on Ketenes Michael Additions Enantioselective Decarboxylative Protonation Proton Migration Summary of Cinchona-Mediated Enantioselective Protonations CINCHONA-CATALYZED NUCLEOPHILIC 1,2-ADDITION TO C=O AND C=N BONDS Introduction Aldol and Nitroaldol (Henry) Reactions Mannich and Nitro-Mannich Reactions Aldol- and Mannich-Related Reactions Cyanation Reactions Trifluoromethylation Friedel-Crafts Type Alkylation Hydrophosphonylation Conclusions CINCHONA-CATALYZED NUCLEOPHILIC CONJUGATE ADDITION TO ELECTRON-DEFICIENT C=C DOUBLE BONDS Introduction Conjugate Reaction of Alpha,Beta-Unsaturated Ketones, Amides, and Nitriles Conjugate Addition of Nitroalkenes Conjugate Addition of Vinyl Sulfones and Vinyl Phosphates Cyclopropanation and Other Related Reactions Conclusions CINCHONA-CATALYZED CYCLOADDITION REACTIONS Introduction Asymmetric Cycloadditions Catalyzed by Quinuclidine Tertiary Amine Asymmetric Cycloadditions Catalyzed by Bifunctional Cinchona Alkaloids Asymmetric Cycloaddition Reactions Catalyzed by Cinchona-Based Primary Amines Asymmetric Cycloaddition Catalyzed by Cinchona-Based Phase-Transfer Catalysts Conclusion CINCHONA-BASED ORGANOCATALYSTS FOR DESYMMETRIZATION OF MESO-COMPOUNDS AND (DYNAMIC) KINETIC RESOLUTION OF RACEMIC COMPOUNDS Introduction Desymmetrization of meso-Compounds (Dynamic) Kinetic Resolution of Racemic Compounds Conclusions PART III: Organic Chemistry of Cinchona Alkaloids ORGANIC CHEMISTRY OF CINCHONA ALKALOIDS Introduction Preparation of Quincorine and Quincoridine: Discovery of a Novel Cleavage Reaction of Cinchona Alkaloids Transformations of the Quinoline Moiety Basic Transformations of the Vinyl Side Chain Selected Novel Transformations of the Quinuclidine Moiety of Cinchona Alkaloids Nucleophilic Substitution at Carbon C9 Novel Rearrangements of the Azabicyclic Moiety General Experimental Hints and Obstacles Conclusions PART IV: Cinchona Alkaloid and Their Derivatives in Analytics RESOLUTION OF RACEMATES AND ENANTIOSELECTIVE ANALYTICS BY CINCHONA ALKALOIDS AND THEIR DERIVATIVES Introduction Resolution of Racemates by Crystallization and Extraction of Diastereoisomers Enantioselective Chromatography and Related Techniques Cinchona Alkaloids as Chiral Solvating (Shift) Agents in NMR Spectroscopy Cinchona-Based Sensors, Receptors, and Materials for Separation and Analytics