Asymmetric Catalysis on Industrial Scale

Challenges, Approaches and Solutions
 
 
Wiley-VCH (Verlag)
  • 2. Auflage
  • |
  • erschienen am 5. August 2011
  • |
  • XXXVIII, 542 Seiten
 
E-Book | ePUB mit Adobe DRM | Systemvoraussetzungen
978-3-527-64216-8 (ISBN)
 
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.

 
Die zweite Auflage dieser bahnbrechenden Publikation zur industriellen asymmetrischen Katalyse fängt die wichtigsten Trends und aktuellen Entwicklungen ein. Komplett neue Fallstudien weltweit führender Fachleute bieten Ihnen einen kompakten und kompetenten Einblick in das Gesamtgebiet.

2. Auflage
  • Englisch
  • 7
  • |
  • 94 s/w Tabellen, 124 s/w Abbildungen, 7 farbige Abbildungen
  • 9,29 MB
978-3-527-64216-8 (9783527642168)
3527642161 (3527642161)
weitere Ausgaben werden ermittelt
Hans-Ulrich Blaser carried out his doctoral research with A. Eschenmoser at the Federal Institute of Technology (ETH) Zürich, where he received the Ph.D. degree in 1971. Between 1971 and 1975 he held postdoctoral positions at the University of Chicago (J. Halpern), Harvard University (J.A. Osborn), and Monsanto (Zürich). During 20 years at Ciba-Geigy (1976-1996) he gained practical experience at R&D in the fine chemicals and pharmaceutical industry, which continued at Novartis (1996-1999) and at Solvias where he presently is chief technology officer.

Hans-Jürgen Federsel is a renowned specialist in the field of process R&D with a professional career spanning over 30 years. Starting off as bench chemist in Astra at the major Swedish site in Södertälje, he climbed the ranks to occupy positions both as line and project manager. After the merger that formed AstraZeneca, he became Head of Projects Management at the aforementioned location and was then appointed to the newly created role as Director of Science in Global Process R&D in 2004. In connection with this, he was also given the prestigious title Senior Principal Scienstist. His strong academic links have been further developed over the years after obtaining the PhD in Organic Chemistry at the Royal Institute of Technology in Stockholm, which was led to his being awarded an Associate Professorship there.
His long-lasting links to this Institute has brought him a seat on the Board of the School of Chemical Science and Engineering from 2005. Publishing in peer reviewed journals and books and frequent lecturing has rendered fame to his name that goes far beyond the limits of the own company and Dr. Federsel enjoys invitations from all over the world to share learning and experience from his broad knowledge base on process R&D. In 2009 he was elected to the Royal Swedish Academy of Engineering Sciences (IVA).
PART I: New Processes for Existing Active Compounds (APIs)

SOME RECENT EXAMPLES IN DEVELOPING BIOCATALYTIC PHARMACEUTICAL PROCESSES
Introduction
Levetiracetam (Keppra®)
Atorvastatin (Lipitor®)
Pregabalin (Lyrica®)
Conclusion
ENANTIOSELECTIVE HYDROGENATION: APPLICATIONS IN PROCESS R&D OF PHARMACEUTICALS
Introduction
Carbonyl Hydrogenations
Imine Hydrogenation
Conclusion
CHIRAL LACTONES BY ASYMMETRIC HYDROGENATION - A STEP FORWARD IN (+)-BIOTIN PRODUCTION
Introduction: (+)-Biotin as an Example for the Industrial Production of Vitamins
Commercial Syntheses and Other Routes to (+)-Biotin by Total Synthesis
Catalytic Asymmetric Reduction of Cyclic Anhydride to D-Lactone
Conclusion
BIOCATALYTIC ASYMMETRIC OXIDATION FOR THE PRODUCTION OF BICYCLIC PROLINE PEPTIDOMIMETICS
Introduction
Development of Routes to 1 and 2
Asymmetric Biocatalytic Amine Oxidation
Enzyme Evolution - Current State of the Art
Amine Oxidase Evolution
Chemical Development
Optimization of Cyanation
Conclusion
THE ASYMMETRIC REDUCTION OF HETEROCYCLIC KETONES - A KEY STEP IN THE SYNTHESIS OF POTASSIUM-COMPETITIVE ACID BLOCKERS (P-CABs)
Potassium-Competitive Acid Blockers - A New Option for the Treatment of Acid-Related Diseases
Discovery and Development of 7H-8,9-Dihydropyrano[2,3-c]imidazo[1,2-a]pyridines as Potassium-Competitive Acid Blockers
Noyori-Type Catalysts for the Asymmetric Reduction of Prochiral Ketones
Research Overview
Asymmtric Reduction of Ketones Bearing the Imidazo[1,2-a]pyridine Skeleton
Asymmetric Reduction of Ketones Bearing the 3,6,7,8-Tetrahydrochromenol[7,8-d]imidazole Skeleton
Large-Scale Asymmetric Synthesis of the 3,6,7,8-Tetrahydrochromeno[7,8-d]imidazole BYK 405879
Conclusions

PART II: Processes for Important Building Blocks

APPLICATION OF A MULTIPLE-ENZYME SYSTEM FOR CHIRAL ALCOHOL PRODUCTION
Introduction
Construction of an Enzymatic Reduction System
Enzymatic Stereoinversion System
CHEMOENZYMATIC ROUTE TO THE SIDE-CHAIN OF ROSUVASTATIN
Introduction
Route Selection
Process Development
Conclusion
ASYMMETRIC HYDROGENATION OF A 2-ISOPROPYLCINNAMIC ACID DERIVATIVE EN ROUTE TO THE BLOOD PRESSURE-LOWERING AGENT ALISKIREN
Introduction
Development of Monodentate Phosphoramidites as Ligands for Asymmetric Hydrogenation
Instant Ligand Libraries of Monodentate BINOL-Based Phosphoramidites
Aliskiren
High-Throughput Screening in Search of a Cheap Phosphoramidite Ligand
Mixtures of Ligands
Further Screening of Conditions
Validation and Pilot Plant Run
Instant Ligand Library Screening to Further Optimize Rate and ee
Validations
Recent Developments in the Asymmetric Hydrogenation of 3
Conclusion
ASYMMETRIC PHASE-TRANSFER CATALYSIS FOR THE PRODUCTION OF NON-PROTEINOGENIC ALPHA-AMINO ACIDS
Background
Designer's Chiral Phase-Transfer Catalysts
Cynthesis of the C2-Symmetric Chiral Mono-1,1'-Binaphthyl-Derived Catalyst
Application of Enantiomers of 21 to the Industrial Production of NPAAs
Conclusion
DEVELOPMENT OF EFFICIENT TECHNICAL PROCESSES FOR THE PRODUCTION OF ENANTIOPURE AMINO ALCOHOLS IN THE PHARMACEUTICAL INDUSTRY
Introduction
Phenylephrine
Adrenaline (Epinephrine)
Lobeline
Availability of the Catalyst
General Remarks on the Development of Industrial Processes for Asymmetric Hydrogenation
THE ASYMMETRIC HYDROGENATION OF ENONES - ACCESS TO A NEW L-MENTHOL SYNTHESIS
Introduction
Screening of Metal Complexes, Conditions, and Ligands
Scale-Up and Mechanistic Work
Catalyst Recycling and Continuous Processing
Conclusion
ELIMINATING BARRIERS IN LARGE-SCALE ASYMMETRIC SYNTHESIS
Introduction
Improvement of the Synthetic Route to Biaryl Ligands
Development of an Efficient Process En Route to Unprotected Beta-Amino Acids
Conclusion
CATALYTIC ASYMMETRIC RING OPENING: A TRANSFER FROM ACADEMIA TO INDUSTRY
Introduction
Catalyst Preparation and Initial Optimization
Further Optimization
Process Adaptation
Protecting Group Adaption
Use of Benzoate as O-Nucleophile
Chemical Elaboration
Conclusion
ASYMMETRIC BAEYER-VILLIGER REACTIONS USING WHOLE-CELL BIOCATALYSTS
Int

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