This second edition of the pioneering work on this hot topic captures the major trends and latest achievements in the art of asymmetric catalysis on an industrial scale. A number of completely new real-life case studies written by the world leaders in their respective areas provide a compact and qualified insight into this developing field. The resulting ready reference and handbook collates first-hand and valuable information within a context where it can be easily found.
The high-quality contributions illustrate the relevant environments and situations, such as time pressure, how the catalytic step fits into the overall synthesis, or competition with other synthetic approaches, as well as the typical problems encountered in the various phases, including finding/developing the catalyst and optimization of the process or choice of equipment. Both successful and unsuccessful approaches to solve these problems are described.
Language: English
Pages: 562
Tags: Химия и химическая промышленность;Кинетика и катализ;
Content:
Chapter 1 Some Recent Examples in Developing Biocatalytic Pharmaceutical Processes (pages 1–12): Junhua Tao, J. Liu and Z. Chen
Chapter 2 Enantioselective Hydrogenation: Applications in Process R&D of Pharmaceuticals (pages 13–25): Kurt Puntener and Michelangelo Scalone
Chapter 3 Chiral Lactones by Asymmetric Hydrogenation – A Step Forward in (+)?Biotin Production (pages 27–39): Werner Bonrath, Reinhard Karge, Thomas Netscher, Felix Roessler and Felix Spindler
Chapter 4 Biocatalytic Asymmetric Oxidation for the Production of Bicyclic Proline Peptidomimetics (pages 41–60): James J. Lalonde and Jack Liang
Chapter 5 The Asymmetric Reduction of Heterocyclic Ketones – A Key Step in the Synthesis of Potassium?Competitive Acid Blockers (P?CABs) (pages 61–78): Andreas Marc Palmer and Antonio Zanotti?Gerosa
Chapter 6 Application of a Multiple?Enzyme System for Chiral Alcohol Production (pages 79–109): Junzo Hasegawa, Hirokazu Nanba and Yoshihiko Yasohara
Chapter 7 Chemoenzymatic Route to the Side?Chain of Rosuvastatin (pages 111–126): Robert A. Holt and Christopher D. Reeve
Chapter 8 Asymmetric Hydrogenation of a 2?Isopropylcinnamic Acid Derivative en Route to the Blood Pressure?Lowering Agent Aliskiren (pages 127–150): Jeroen A. F. Boogers, Dirk Sartor, Ulfried Felfer, Martina Kotthaus, Gerhard Steinbauer, Bert Dielemans, Laurent Lefort, Andre H. M. de Vries and Johannes G. de Vries
Chapter 9 Asymmetric Phase?Transfer Catalysis for the Production of Non?Proteinogenic ??Amino Acids (pages 151–169): Masaya Ikunaka and Keiji Maruoka
Chapter 10 Development of Efficient Technical Processes for the Production of Enantiopure Amino Alcohols in the Pharmaceutical Industry (pages 171–185): Franz Dietrich Klingler
Chapter 11 The Asymmetric Hydrogenation of Enones – Access to a New L?Menthol Synthesis (pages 187–205): Christoph Jakel and Rocco Paciello
Chapter 12 Eliminating Barriers in Large?Scale Asymmetric Synthesis (pages 207–218): Hideo Shimizu, Noboru Sayo and Takao Saito
Chapter 13 Catalytic Asymmetric Ring Opening: A Transfer from Academia to Industry (pages 219–229): Dirk Spielvogel
Chapter 14 Asymmetric Baeyer–Villiger Reactions Using Whole?Cell Biocatalysts (pages 231–248): Roland Wohlgemuth and John M. Woodley
Chapter 15 Large?Scale Applications of Hydrolases in Biocatalytic Asymmetric Synthesis (pages 249–264): Roland Wohlgemuth
Chapter 16 Scale?Up Studies in Asymmetric Transfer Hydrogenation (pages 265–290): A. John Blacker and Peter Thompson
Chapter 17 2,2?,5,5??Tetramethyl?4,4??bis(diphenylphoshino)?3,3??bithiophene: A Very Efficient Chiral Ligand for Ru?Catalyzed Asymmetric Hydrogenations on the Multi?Kilograms Scale (pages 291–299): Oreste Piccolo
Chapter 18 The Power of Whole?Cell Reaction: Efficient Production of Hydroxyproline, Sugar Nucleotides, Oligosaccharides, and Dipeptides (pages 301–320): Shin?Ichi Hashimoto, Satoshi Koizumi and Akio Ozaki
Chapter 19 Enantioselective Ketone Hydrogenation: From Research to Pilot Scale with Industrially Viable Ru–(Phosphine–Oxazoline) Complexes (pages 321–329): Frederic Naud, Felix Spindler, Carsten Rueggeberg, Andreas T. Schmidt and Dr. Hans?Ulrich Blaser
Chapter 20 Enabling Asymmetric Hydrogenation for the Design of Efficient Synthesis of Drug Substances (pages 331–376): Yongkui Sun, Shane Krska, C. Scott Shultz and David M. Tellers
Chapter 21 Scale?Up of a Telescoped Enzymatic Hydrolysis Process for an Intermediate in the Synthesis of a Factor Xa Inhibitor (pages 377–396): Hans Iding, Beat Wirz, Jean?Michel Adam, Pascal Dott, Wolfgang Haap, Rosa Maria Rodriguez Sarmiento, Thomas Oberhauser, Reinhard Reents, Rolf Fischer and Stephan Lauper
Chapter 22 An Efficient, Asymmetric Synthesis of Odanacatib, a Selective Inhibitor of Cathepsin K for the Treatment of Osteoporosis, Using an Enzyme?Mediated Dynamic Kinetic Resolution (pages 397–414): Matthew D. Truppo
Chapter 23 Biocatalytic Routes to the GPIIb/IIIa Antagonist Lotrafiban, SB 214857 (pages 415–437): Andy Wells
Chapter 24 Discovery and Development of a Catalytic Asymmetric Conjugate Addition of Ketoesters to Nitroalkenes and Its Use in the Large?Scale Preparation of ABT?546 (pages 439–455): David M. Barnes
Chapter 25 The Kagan Oxidation – Industrial?Scale Asymmetric Sulfoxidations in the Synthesis of Two Related NK1/NK2 Antagonists (pages 457–471): David R. J. Hose, Bharti Patel, Sharon A. Bowden and Jonathan D. Moseley
Chapter 26 Large?Scale Application of Asymmetric Phase?Transfer Catalysis for Amino Acid Synthesis (pages 473–484): Daniel E. Patterson, Shiping Xie, Lynda A. Jones, Martin H. Osterhout, Christopher G. Henry and Thomas D. Roper
Chapter 27 Application of Phase?Transfer Catalysis in the Organocatalytic Asymmetric Synthesis of an Estrogen Receptor Beta?Selective Agonist (pages 485–497): Jeremy P. Scott
Chapter 28 Asymmetric Synthesis of HCV and HPV Drug Candidates on Scale: The Choice between Enantioselective and Diastereoselective Syntheses (pages 499–522): Jeremy D. Cobb, Bob E. Cooley, Roy C. Flanagan, Mary M. Jackson, Lynda A. Jones, Richard T. Matsuoka, Alan Millar, Daniel E. Patterson, Matthew J. Sharp, Jennifer F. Toczko, Shiping Xie and Xiaoming Zhou
