664 pages | 162 B/W Illus.
As pharmaceutical companies look to develop single enantiomers as drug candidates, chemists are increasingly faced with the problems associated with this subclass of organic synthesis. "The Handbook of Chiral Chemicals, Second Edition" highlights the problems associated with the production of chiral compounds on a commercial scale. The handbook first elaborates upon starting materials obtained from a 'chiral pool', which can be derived from natural products. Then it explains methods and reactions that can introduce or influence stereogenic centers, particularly asymmetric hydrogenations, oxidations, pericyclic reactions, and enzymatic methods.While hydrogenations have been the most widely employed approach for the large-scale synthesis of several commercial compounds, the search for the ideal catalyst has consistently led researchers to enzymes present in biological systems. Several chapters concentrate on understanding how to manipulate enzymes for catalyzing new reactions for taking new substrates. Other significant topics include chiral auxiliaries, chromatographic techniques, enantiomers-specific reactions, and resolution. This second edition updates all its chapters, illustrating the speed of development in this field, and features new chapters that highlight successful approaches in an industrial setting. "The Handbook of Chiral Chemicals, Second Edition" is a guide to advances in the field that result in more efficient and cost-effective synthesis of chiral chemicals.
"The fifty-four contributors have produced a fine volume, clear and precise with plentiful diagrams, tables and formulae to aid the reader. Each chapter is profusely referenced and substantial index permits a reader to find what they are looking for. The book is well made . . . If you are involved with chiral compounds this book is a must for your library."
– Steve Mitchell, Faculty of Medicine, Imperial College London, in Newsletter of Science, Technology & Medicine, Summer 2008, Vol. 28, No. 2
1. Introduction 2. Amino Acids 3. Microbial Pathway Engineering for Amino Acid Manufacture 4. Carbohydrates in Synthesis 5. Terpenes: The Expansion of the Chiral Pool 6. Resolutions at Large Scale: Case Studies 7. New Developments in Crystallization-Induced Resolution 8. The Role of cis-1-Amino-2-Indanol in Resolution Processes 9. Asymmetric Oxidations 10. Asymmetric Epoxidation of Olefins by Chiral Ketones 11. Ozonolysis in the Production of Chiral Fine Chemicals 12. Transition Metal Catalyzed Hydrogenations, Isomerizations, and Other Reactions 13. Modular, Chiral P-Heterocycles in Asymmetric Catalysis 14. Asymmetric Olefin Hydrogenation Using Monodentate BINOL- and Bisphenol-Based Ligands: Phosphonites, Phosphites, and Phosphoramidites 15. Asymmetric Catalytic Hydrogenation Reactions with Ferrocene-Based Diphosphine Ligands 16. Asymmetric Reduction of Prochiral Ketones Catalyzed by Oxazaborolidines 17. cis-1-Amino-2-Indanol-Derived Ligands in Asymmetric Catalysis 18. Enantioselective Hydrogenation of Activated Ketones Using Heterogeneous Pt Catalysts Modified with Cinchona Alkaloids 19. Biotransformations: “Green” Processes for the Synthesis of Chiral Fine Chemicals 20. Combining Enzyme Discovery and Evolution to Develop Biocatalysts 21. One-Pot Synthesis and the Integration of Chemical and Biocatalytic Conversions 22. Substitution Reactions 23. Industrial Applications of Chiral Auxiliaries 24. The Role and Importance of cis-1-Amino-2-Indanol in Biological Systems and Asymmetric Processes 25. Enantiopure Amines by Chirality Transfer Using (R)-Phenylglycine Amide 26. Pericyclic Reactions 27. Asymmetric Free-Radical Reductions Mediated by Chiral Stannanes, Germanes, and Silanes 28. Metathesis Reactions 29. Synthesis of Homochiral Compounds: A Small Company’s Role 30. Commercial Synthesis of the Antiglaucoma Prostanoid Travoprost 31. Synthesis of Large Volume Products