rganic Synthesis Highlights III

Transcription

1 rganic Synthesis Highlights III Edited by Johann Mulzer and Herbert Waldmann WILEY-VCH Weinheim New York Chichester Brisbane Singapore Toronto

2 Part I. New Methods and Reagents for Organic Synthesis A. Asymmetrie Synthesis Catalytic Asymmetrie Synthesis Using New Enolato-, Amido-, and Organolithium Chemistry 3 David J. Berrisford, Carlos Horkan, and Matthew L. Isherwood Steric and Stereoelectronic Effects in the Palladium Catalyzed Allylation 8 Asymmetrie Alkylation of Amide Enolates with Pseudoephedrine as Chiral Auxiliary - Unexpected Influence of Additives? 15 Karola Rück-Braun Catalytic Asymmetrie Carbonyl-Ene Reactions 23 David J. Berrisford and Carsten Bolm Chiral 2-Amino-l,3-butadienes: New Reagents for Asymmetrie Cycloadditions 28 Karsten Krohn Recent Developments in the Enantioselective Syntheses of Cyclopropanes 35 Hans-Ulrich Reissig Enantioselective Rhodium(II) Catalysts 40 Henri Brunner Oxazaborolidines and Dioxaborolidines in Enantioselective Catalysis 44 B. B. Lohray, and Vidya Bhushan Enantioselective Catalytic Hydrogenation 51 Judith Albrecht and Ulrich Nagel The Sharpless Asymmetrie Aminohydroxylation of Olefins 57 Epoxides in Asymmetrie Synthesis: Enantioselective Opening by Nueleophiles Promoted by Chiral Transition Metal Complexes 62 lan Paterson and David J. Berrisford

3 VIII Asymmetrie Deprotonation as an Efficient Enantioselective Preparation of Functionalized Secondary Alcohols and Amino-Alcohols 67 Paul Knöchel Planar-Chiral Ferrocenes: Synthetic Methods and Applications 73 Antonio Togni Asymmetrie Autocatalysis with Amplification of Chirality 79 Carsten Bolm, Andreas Seger, and Frank Bienewald Resolution of Racemates by Distillation with Inclusion Compounds 84 Absolute Asymmetrie Synthesis by Irradiation of Chiral Crystals 89 and Michael Haak B. Organometallic Reagents Cyclopentadienyl Ruthenium Complexes: Valuable Assistents in the Construction of Carbon-Carbon Bonds 96 Holger Butenschön Transition Metal Catalyzed Synthesis of Seven-Membered Carbocyclic Rings 103 Gerald Dyker [4+4]-Cycloaddition Reactions in the Total Synthesis of Naturally Occurring Eight-Membered Ring Compounds 106 "New" Reagents for the "Old" Pinacol Coupling Reaction 113 Thomas Wirth Exciting Results from the Field of Homogeneous Two-Phase Catalysis 119 Boy Cornils Palladium-Catalyzed Amination of Aryl Halides 126 Matthias Beller and Thomas H. Riermeier The Metal-mediated Oxidation of Organic Substrates via Organometallic Intermediates: Recent Developments and Questions of Dispute 133 Jörg Sundermeyer The Oxofunctionalization of Alkanes 140 Cooperativity in Rh 2 Complexes: High Catalytic Activity and Selectivity in the Hydroformylation of Olefins 146 Georg Süss-Fink Synthesis of Optically Active Macromolecules Using Metallocene Catalysts 153 Jun Okuda C. Biological and Biomimetic Methods Discovering Biosynthetic Pathways - A Never Ending Story 156 Sabine Laschat and Oliver Temme Peptide Ligases - Tools for Peptide Synthesis 167 Hans-Dieter Jakubke

4 IX Synthetic Ribozymes and Deoxyribozymes 173 Petra Burgstaller and Michael Famulok Enzyme Mimics 185 Anthony J. Kirby Metal-Assisted Peptide Organization: From Coordination Chemistry to De Novo Metalloproteins 192 Heinz-Bernhard Kraatz Artificial Replication Systems 198 Siegfried Hoffmann D. General Methods and Reagents UCIO4 and Organic Solvents - Unusual Reaction Media 205 Uschi Schmid and Herbert Waldmann Reactions in Supercritical Carbon Dioxide 211 The Selective Blocking of fraras-diequatorial, Vicinal Diols; Applications in the Synthesis of Chiral Building Blocks and Complex Sugars 222 Thomas Ziegler Oxidative Polycyclization Versus the "Polyepoxide cascade": New Pathways in Polyether (Bio)synthesis? 230 Radical Reactions as Key Steps in Natural Product Synthesis 235 Light-Directed Parallel Synthesis of Up to Different Oligopeptides and Oligonucleotides 242 Günter von Kiedrowski Opportunities for New Chemical Libraries: Unnatural Biopolymers and Diversomers. 245 Rob M. J. Liskamp Reactive Intermediates 250 Henning Hopf Part II. Applications in Total Synthesis Synthesis of Natural and Non-natural Products Pentazole and Other Nitrogen Rings 265 Rudolf Janoschek New Total Syntheses of Strychnine 270 Uwe Beifuss Total Syntheses of Zaragozic Acid 282 The First Total Syntheses of Taxol 295 Ludger A. Wessjohann

5 X Erythromycin Synthesis - A Never-ending Story? 306 Johann Mulzer Great Expectations for a Total Synthesis of Vancomycin 314 Kevin Burgess, Dongyeol Lim, and Carlos I. Martinez The Dimeric Steroid-Pyrazine Marine Alkaloids: Challenges for Isolation, Synthesis, and Biology 318 Arasu Ganesan New, efficient routes to cyclic enediynes 327 B. König Conocurvone - Prototype of a New Class of Anti-HIV Active Compounds? 331 Hartmut Laatsch Progress in Oligosaccharide Synthesis through a New Orthogonal Glycosylation Strategy 336 Hans Paulsen Analogues of the Sialyl Lewis x Group and of the N-Acetylneuraminic Acid in the Antiadhesion Therapy 342 Athanassios Giannis Peptidomimetics: Modern Approaches and Medical Perspectives 354 Athanassios Giannis A New Application of Modified Peptides and Peptidomimetics: Potential Anticancer Agents 366 R. M. J. Liskamp Mechanically-Interlocked Molecular Systems Incorporating Cyclodextrins 374 Sergey A. Nepogodiev and J. Fräser Stoddart Bolaamphiphiles: Golf Balls to Fibers 382 Gregory H. Escamilla and George R. Newkome Dendrimers, Arborols, and Cascade Molecules: Breakthrough into Generations of New Materials 391 Andreas Archut, Jörg Issberner and Fritz Vögtle Carboranes, Anti-Crowns, Big Wheels, and Supersandwiches 406 Russell N. Grimes Framework Modifications of [60]Fullerene: Cluster Opening Reactions and Synthesis of Heterofullerenes 415 Andreas Hirsch