Asymmetric Synthesis with Chemical and Biological Methods

Asymmetric Synthesis with Chemical and Biological Methods

By: Dieter Enders (editor), Karl-Erich Jaeger (editor), Gunter Helmchen (foreword_author)Hardback

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Description

Edited by two of the leading researchers in the field, this book provides a deep, interdisciplinary insight into stoichiometric and catalytic reactions in this continuously expanding area. A plethora of top German scientists with an international reputation covers various aspects, from classical organic chemistry to process development, and from the theoretical background to biological methods using enzymes. Throughout the focus is on the development of new synthetic methods in asymmetric synthesis, the synthesis of natural and bioactive compounds and the latest developments in both chemical and biological methods of catalysis, as well as the investigation of special technical and biotechnical aspects.

About Author

Dieter Enders completed his PhD at the Justus-Liebig-Universitat Giessen under the supervision of D. Seebach. After postdoctoral studies at Harvard University with E. J. Corey, he returned to Giessen and completed his habilitation. He became Associate Professor at the Universitat Bonn in 1980, and moved to his present position as Professor of Organic Chemistry at the RWTH Aachen in 1985. He has received many awards (Leibniz-Prize of the DFG, Emil Fischer Medal of the GDCh, Yamada Prize, Japan) for his research, which focuses on the asymmetric synthesis of biologically active compounds and the development of new synthetic methods. Karl-Erich Jaeger was born in Dortmund and studied biology and chemistry at the Ruhr-University Bochum, where he received his PhD under the supervision of U. Winkler. After postdoctoral studies with Robert E.W. Hancock at the Department of Microbiology of the University of British Columbia in Vancouver, he received his habilitation in Bochum in 1995. Karl-Erich Jaeger is currently Professor at the Heinrich-Heine University of Dusseldorf and Director of the Institute of Molecular Enzyme Technology at the Research Centre Julich. His research interests include the expression, folding and secretion of bacterial enzymes, their optimization by directed evolution, and enantioselective biocatalysis.

Contents

Foreword. Preface. List of Contributors. 1 Stoichiometric Asymmetric Synthesis. 1.1 Development of Novel Enantioselective Synthetic Methods (Dieter Enders and Wolfgang Bettray). 1.1.1 Introduction 1 1.1.2 alpha-Silyl Ketone-Controlled Asymmetric Syntheses. 1.1.3 Asymmetric Hetero-Michael Additions. 1.1.4 Asymmetric Syntheses with Lithiated alpha-Aminonitriles. 1.1.5 Asymmetric Electrophilic alpha-Substitution of Lactones and Lactams. 1.1.6 Asymmetric Synthesis of alpha-Phosphino Ketones and 2-Phosphino Alcohols. 1.1.7 Asymmetric Synthesis of 1,3-Diols and anti-1,3-Polyols. 1.1.8 Asymmetric Synthesis of alpha-Substituted Sulfonamides and Sulfonates. 1.2 Asymmetric Synthesis of Natural Products Employing the SAMP/RAMP Hydrazone Methodology (Dieter Enders and Wolfgang Bettray). 1.2.1 Introduction. 1.2.2 Stigmatellin A. 1.2.3 Callistatin A. 1.2.4 Dehydroiridodiol(dial) and Neonepetalactone. 1.2.5 First Enantioselective Synthesis of Dendrobatid Alkaloids Indolizidine 209I and 223J. 1.2.6 Effi cient Synthesis of (2S,12'R)-2-(12'-Aminotridecyl)pyrrolidine, a Defense Alkaloid of the Mexican Bean Beetle. 1.2.7 2-epi-Deoxoprosopinine. 1.2.8 Attenol A and B. 1.2.9 Asymmetric Synthesis of (+)- and (-)-Streptenol A. 1.2.10 Sordidin. 1.2.11 Prelactone B and V. 1.3 Asymmetric Synthesis Based on Sulfonimidoyl-Substituted Allyltitanium Complexes (Hans-Joachim Gais). 1.3.1 Introduction. 1.3.2 Hydroxyalkylation of Sulfonimidoyl-Substituted Allylltitanium Complexes. 1.3.3 Aminoalkylation of Sulfonimidoyl-Substituted Allyltitanium Complexes. 1.3.4 Structure and Reactivity of Sulfonimidoyl-Substituted Allyltitanium Complexes. 1.3.5 Asymmetric Synthesis of Homopropargyl Alcohols. 1.3.6 Asymmetric Synthesis of 2,3-Dihydrofurans. 1.3.7 Synthesis of Bicyclic Unsaturated Tetrahydrofurans. 1.3.8 Asymmetric Synthesis of Alkenyloxiranes. 1.3.9 Asymmetric Synthesis of Unsaturated Mono- and Bicyclic Prolines. 1.3.10 Asymmetric Synthesis of Bicyclic Amino Acids. 1.3.11 Asymmetric Synthesis of beta-Amino Acids. 1.3.12 Conclusion. 1.4 The "Daniphos" Ligands: Synthesis and Catalytic Applications (Albrecht Salzer and Wolfgang Braun). 1.4.1 Introduction. 1.4.2 General Synthesis. 1.4.3 Applications in Stereoselective Catalysis. 1.4.4 Conclusion. 1.5 New Chiral Ligands Based on Substituted Heterometallocenes (Christian Ganter). 1.5.1 Introduction. 1.5.2 General Properties of Phosphaferrocenes. 1.5.3 Synthesis of Phosphaferrocenes. 1.5.4 Preparation of Bidentate P,P and P,N Ligands. 1.5.5 Modifi cation of the Backbone Structure. 1.5.6 Cp-Phosphaferrocene Hybrid Systems. 1.5.7 Catalytic Applications. 1.5.8 Conclusion. 2 Catalytic Asymmetric Synthesis. 2.1 Chemical Methods. 2.1.1 Sulfoximines as Ligands in Asymmetric Metal Catalysis (Carsten Bolm). 2.1.2 Catalyzed Asymmetric Aryl Transfer Reactions (Carsten Bolm). 2.1.3 Substituted [2.2]Paracyclophane Derivatives as Effi cient Ligands for Asymmetric 1,2- and 1,4-Addition Reactions (Stefan Brase). 2.1.4 Palladium-Catalyzed Allylic Alkylation of Sulfur and Oxygen Nucleophiles - Asymmetric Synthesis, Kinetic Resolution and Dynamic Kinetic Resolution (Hans-Joachim Gais). 2.1.5 The QUINAPHOS Ligand Family and its Application in Asymmetric Catalysis (Giancarlo Francio, Felice Faraone, and Walter Leitner). 2.1.6 Immobilization of Transition Metal Complexes and Their Application to Enantioselective Catalysis (Adrian Crosman, Carmen Schuster, Hans-Hermann Wagner, Melinda Batorfi , Jairo Cubillos, and Wolfgang Holderich). 2.2 Biological Methods. 2.2.1 Directed Evolution to Increase the Substrate Range of Benzoylformate Decarboxylase from Pseudomonas putida (Marion Wendorff, Thorsten Eggert, Martina Pohl, Carola Dresen, Michael Muller, and Karl-Erich Jaeger). 2.2.2 C-C-Bonding Microbial Enzymes: Thiamine Diphosphate-Dependent Enzymes and Class I Aldolases (Georg A. Sprenger, Melanie Schurmann, Martin Schurmann, Sandra Johnen, Gerda Sprenger, Hermann Sahm, Tomoyuki Inoue, and Ulrich Schorken). 2.2.3 Enzymes for Carboligation - 2-Ketoacid Decarboxylases and Hydroxynitrile Lyases (Martina Pohl, Holger Breittaupt, Bettina Frolich, Petra Heim, Hans Iding, Bettina Juchem, Petra Siegert, and Maria-Regina Kula). 2.2.4 Preparative Syntheses of Chiral Alcohols using (R)-Specifi c Alcohol Dehydrogenases from Lactobacillus Strains (Andrea Weckbecker, Michael Muller, and Werner Hummel). 2.2.5 Biocatalytic C-C Bond Formation in Asymmetric Synthesis (Wolf-Dieter Fessner). 2.2.6 Exploring and Broadening the Biocatalytic Properties of Recombinant Sucrose Synthase 1 for the Synthesis of Sucrose Analogues (Lothar Elling). 2.2.7 Flexible Asymmetric Redox Reactions and C-C Bond Formation by Bioorganic Synthetic Strategies (Michael Muller, Michael Wolberg, Silke Bode, Ralf Feldmann, Petra Geilenkirchen, Thomas Schubert, Lydia Walter, Werner Hummel, Thomas Dunnwald, Ayhan S. Demir, Doris Kolter-Jung, Adam Nitsche, Pascal Dunkelmann, Annabel Cosp, Martina Pohl, Bettina Lingen, and Maria-Regina Kula). 3 Reaction Technology in Asymmetric Synthesis. 3.1 Reaction Engineering in Asymmetric Synthesis (Stephan Lutz, Udo Kragl, Andreas Liese, and Christian Wandrey). 3.1.1 Introduction. 3.1.2 Membrane Reactors with Chemical Catalysts. 3.1.3 Membrane Reactors with Biological Catalysts. 3.1.4 Two-Phase Systems. 3.1.5 Conclusions. 3.2 Biocatalyzed Asymmetric Syntheses Using Gel-Stabilized Aqueous-Organic Two-Phase Systems (Marion B. Ansorge-Schumacher). 3.2.1 Gel-Stabilized Two-Phase Systems. 3.2.2 Benzoin Condensation with Entrapped Benzaldehyde Lyase. 3.2.3 Reduction of Ketones with Entrapped Alcohol Dehydrogenase. 3.2.4 Conclusion. Index. Name Index.

Product Details

  • ISBN13: 9783527314737
  • Format: Hardback
  • Number Of Pages: 470
  • ID: 9783527314737
  • weight: 1047
  • ISBN10: 3527314733

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