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 α-Silyl Ketone-Controlled Asymmetric Syntheses.

1.1.3 Asymmetric Hetero-Michael Additions.

1.1.4 Asymmetric Syntheses with Lithiated α-Aminonitriles.

1.1.5 Asymmetric Electrophilic α-Substitution of Lactones and Lactams.

1.1.6 Asymmetric Synthesis of α-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 α-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 β-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 Bräse).

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 Franciò, 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 Hölderich).

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 Müller, and Karl-Erich Jaeger).

2.2.2 C–C-Bonding Microbial Enzymes: Thiamine Diphosphate-Dependent Enzymes and Class I Aldolases (Georg A. Sprenger, Melanie Schürmann, Martin Schürmann, Sandra Johnen, Gerda Sprenger, Hermann Sahm, Tomoyuki Inoue, and Ulrich Schörken).

2.2.3 Enzymes for Carboligation – 2-Ketoacid Decarboxylases and Hydroxynitrile Lyases (Martina Pohl, Holger Breittaupt, Bettina Frölich, 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 Müller, 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 Müller, Michael Wolberg, Silke Bode, Ralf Feldmann, Petra Geilenkirchen, Thomas Schubert, Lydia Walter, Werner Hummel, Thomas Dünnwald, Ayhan S. Demir, Doris Kolter-Jung, Adam Nitsche, Pascal Dünkelmann, Annabel Cosp, Martina Pohl, Bettina Lingen, and Maria-Regina Kula).

3 Reaction Technology in Asymmetric Synthesis.

3.1 Reaction Engineering in Asymmetric Synthesis (Stephan Lütz, 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.