Holdings: Asymmetric synthesis

Asymmetric synthesis: the essentials

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Bibliographic Details
Format:	Book
Language:	English
Published:	Weinheim WILEY-VCH 2008
Edition:	2., completely rev. ed.
Subjects:	Chiraliteit Enantiomeren Stereochemie Stereoselectiviteit Synthese (chemie) Asymmetric synthesis Asymmetrische Synthese Aufsatzsammlung
Online Access:	http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm Inhaltsverzeichnis Klappentext
Item Description:	Literaturangaben
Physical Description:	XL, 355 S. Ill., graph. Darst.
ISBN:	9783527320936

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adam_text	IX Contents Foreword V Message from the Editors XXV List of Abbreviations XXVII Named and Unnamed Reactions XXXI List of Contributors XXXIII Part I Chiral Auxiliaries in Asymmetric Synthesis Introductory Chapter 3 David A. Evans, Günter Helmchen and Magnus Raping Background 3 Results 4 Summary 7 CV of David A. Evans 8 CV of Günter Helmchen S CV of Magnus Rüping 9 Selected Publications 9 Asymmetric Epoxidation of Pentadienols 10 Reinhard Bruckner Background 10 Objective: Making Building Blocks for the Synthesis of 1,3,5,7,— -Polyols from Epoxyalcohols 11 Results 12 Asymmetric Epoxidation of a Conjugated Pentadienol 12 Asymmetric Epoxidation of a Nonconjugated Pentadienol 13 CV of Reinhard Bruckner IS Selected Publications 16 X Contents Asymmetrie Synthesis using Sulfur-Nitrogen Reagents 17 Franklin A. Davis Background 17 Results 17 Asymmetric Oxidations using N-Sulfonyloxaziridines 17 Asymmetric Fluorination of Enolates with N-Fluoro^lO-Camphorsultams 19 Asymmetric Synthesis of Amine Derivatives using Enantiopure Sulfinimines (N-Sulfinyl Imines) 19 Outlook 20 CV of Franklin A. Davis 20 Selected Publications 22 Asymmetric Syntheses with SAMP^RAMP-Hydrazones 23 Dieter Enders and Wolfgang Bettray Background 23 Strategy 24 Results 25 Application for the Synthesis of Natural Products 26 Other Asymmetric Syntheses from the Enders Group 27 Conclusions and Future Perspectives 27 CV of Dieter Enders 27 Selected Publications 28 Asymmetric Allylation Reactions 29 Reinhard W. Hoffmann Background 29 Results 29 Type (I) Allylmetallation of Aldehydes 29 Second Generation Allylmetallation Reagents 31 CV of Reinhard W. Hoffmann 32 Selected Publications 33 Carbohydrates as Chirai Auxiliaries 34 Horst Kunz Introduction 34 Results 34 Carbohydrate Auxiliaries in Cycloaddition Reactions 34 Conjugate Addition Reactions Directed by Carbohydrate Auxiliaries 35 Glycosylamines in Stereoselective Synthesis 36 Conclusions 38 CV of Horst Kunz 38 Selected Publications 38 Contents XI The Use of Chiral Oxazolines in early C -С Bond Forming Reactions 39 Albert I. Meyers Background 39 Results 40 CV of Albert I. Meyers 41 Selected Publications 41 Asymmetric Synthesis of Amines and Amino Acids from Amines 42 Shun-Ichi Murahashi and Yasushi Imada Background 42 Strategy 43 Results 43 Diastereoselective Reactions of Nitrones 43 Enantioselective Reactions of Nitrones 44 Conclusions and Future Perspectives 46 CV of Shun-Ichi Murahashi 46 Selected Publications 47 Part II Metal-catalyzed Asymmetric Synthesis Introductory Chapter 51 Masakatsu Shibasaki and Shigeki Matsunaga Introduction 51 Design of Asymmetric Metal Catalysis 52 Future Prospects for Metal-catalyzed Asymmetric Synthesis 53 CV of Masakatsu Shibasaki 54 CV of Shigeki Matsunaga 54 Selected Publications 55 Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds 56 Varinder Aggarwal Background 56 Results 57 Other Reactions of Sulfur Ylides from the Aggarwal Group 59 Conclusions and Future Perspectives 59 CV of Varinder Aggarwal 60 Selected Publications 61 XII Contents Asymmetrie Baeyer-Villiger Reactions 62 Carsten Bolm Background 62 Strategy 63 Results 64 Other Research Topics from the Bolm Group 65 CV of Carsten Bolm 65 Selected Publications 66 Planar Chiral Ligands Based on p^JParacyclophanes 67 Stefan Bräse Background 67 Strategy 68 Results 69 Application for the Synthesis of Natural Products 70 Other Asymmetric Syntheses from the Bräse Group 70 Conclusions and Future Perspectives 71 CV of Stefan Bräse 71 Selected Publications 71 Asymmetric Syntheses of S-jtrans^-NitrocydopropylJalanine and S-jtrans^-AminocydopropylJalanine 72 Armin de Majere ană Oleg V. Larionov Background 72 Strategy and Results 73 Outlook 75 CV of Armin de Meijere 75 CV of Oleg V Larionov 76 Selected Publications 76 Copper-Bisjoxazoline) Catalyzed Synthesis of ß-Lactams - Enantioseiective Reaction of Alkynes with Nitrones 77 David A. Evans, Florian Kleinbeck and Magnus Rüping Background 77 Results 78 Summary 80 CV of David A. Evans 81 CV of Magnus Rüping 82 CV of Florian Kleinbeck 81 Selected Publications 81 Contents XIII Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents 83 Fernando López and Ben L. Veringa Background 83 The First Catalytic Enantioselective Approaches 83 Results 84 Cu-catalyzed Enantioselective CA of Organozinc Reagents 84 Highly Enantioselective Cu-catalyzed CA of Grignard Reagents 86 Conclusion and Future Perspectives 87 CV of Fernando López 87 CV of Ben L. Feringa 88 Selected Publications 88 Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution 90 Hans-Joachim Gais Introduction 90 Strategy 91 Results 91 Application to the Synthesis of Natural Products 94 Other Asymmetric Syntheses from the Gais Group 94 Conclusion and Future Perspectives 94 CV of Hans-Joachim Gais 94 Selected Publications 95 Asymmetric Cross-coupling Reactions 97 Tamio Hayashi Background 97 Results 97 Asymmetric Cross-coupling of Secondary Alkyl Grignard Reagents 97 Asymmetric Cross-Coupling Forming Axially Chiral Biaryls 99 Conclusions and Future Perspectives 100 CV of Tamio Hayashi 101 Selected Publications 101 Asymmetric Allylic Substitutions 102 Günter Heimchen Background 102 Results 103 Pd-Catalyzed Aliylic Substitutions 103 ir-Catalyzed Allylic Substitutions 104 Application for the Synthesis of Biologically Active Compounds 104 Other Asymmetric Syntheses from the Helmchen Group 205 Conclusions and Future Perspectives 105 CV of Günter Helmchen 105 Selected Publications 106 XIV Contents Asymmetrie Homoatdol Reactions 107 Dieter Hoppe Background 107 Results 208 Enantioselective Additions via Stereospecific Deprotonation 108 Enantìoselectìve Additions via (-J-Sparteine-mediated ct-Deprotonations 109 Enantioselective γ -Deprotonations 110 Synthetic Applications 110 CV of Dieter Hoppe 22 2 Selected Publications 222 Asymmetric Vinylogous Mukaiyama Aldol Reaction 222 Markus Katesse and Jorma Hassfeld Introduction 222 Results 112 Conclusions and Further Perspectives 225 CV of Markus Kaiesse 116 CV of Jorma Hassfeld 2 2 б Selected Publications 226 Chiral Lewis Acid Catalysis in Aqueous Media 117 Shu Kobayashi and Chikako Ogawa Background 227 Results 117 Water-compatible Lewis Acid 227 Asymmetric Aldol Reactions 228 Asymmetric Hydroxymethylatkm Reactions 229 Asymmetric Mannich-type Reactions 220 CV of Shu Kobayashi 222 CV of Chikako Ogawa 222 Selected Publications 222 Asymmetric Epoxidation of Non-activated Olefins 123 Kazuhiro Matsumoto and Tsutomu Katsuki Introduction 223 Results 223 Manganese(salen) Catalyst 223 Ruthenium(salen) Catalyst 224 Titanium(salalen) Catalyst 225 Conclusion 126 CV of Tsutomu Katsuki 227 CV of Kazuhiro Matsumoto 127 Selected Publications 227 Contents XV Chiral Carbonyl Lewis Acid Complexes in Asymmetrie Syntheses 128 Keiji Maruoka and Takashi Ooi Background 128 Results 128 Conclusions and Future Perspectives 131 CV of Keiji Maruoka 131 CV of Takashi Ooi 131 Selected Publications 132 ZACA Reaction: Zr-catalyzed Asymmetric Carboalumination of Alkenes 133 Ei-ichi Negishi, Bo Liang, Tibor Novak and Ze Tan Background and Discovery 133 Results 134 ZACA-Pd-catalyzed Cross-coupling Tandem Processes for the Synthesis of Deoxypolypropionates and Related Compounds 134 Synthesis of 2 -Methyl- or 2-Eťhyl-l-alkanols Not Readily Purifiable by Chromatography or Recrystallization 137 CV of Ei-ichi Negishi 137 Selected Publications 138 Bisoxazolines - a Privileged Ligand Class for Asymmetric Catalysis 139 Andreas Pfaltz Background 139 Results 140 Semicorrins 140 C2 -Symmetric Bisoxazolines 140 Boron-bridged Bisoxazolines 142 Conclusion 142 CV of Andreas Pfaltz 142 Selected Publications 143 Enantioselective Cycloaddition Reactions Catalyzed by Hydrogen Bonding 144 Viresh H. Rawal and Avinash N. Thadani Background 144 Strategy 146 Results 146 Application to Other Reactions 147 Conclusions and Future Perspectives 147 CV of Viresh H. Rawal 147 Selected Publications 148 XVI Contents Direct Catalytic Asymmetric Aldol-Tishchenko Reaction 149 Masakatsu Shibasaki and Takashi Ohshima Background 349 Strategy 150 Results 150 Mechanistic Studies 152 Conclusions and Future Perspectives 253 CV of Masakatsu Shibasaki 153 CV of Takashi Ohshima 153 Selected Publications 154 Asymmetric Heck and other Palladium-catalyzed Reactions 155 Lutz F. Tietze and Florian Lotz Background 155 Enantioselective Heck Reactions with Allylsilanes as the Alkene Component 155 CV of Lutz F. Tietze 159 CV of Florian Lotz 159 Selected Publications 160 Asymmetric Catalysis with Chiral Acid 162 Hisashi Yamamoto Background 161 Results 162 C2 Symmetric Chiral Lewis Acid Catalysts 162 Combined Acid Catalyst 162 CV of Hisashi Yamamoto 165 Selected Publications 165 Part III Biocatalysis and Organocatalysis: Asymmetric Synthesis Inspired by Nature Introductory Chapter 169 Benjamin List Introduction 169 The Aldol Reaction as an Example 269 Asymmetric Chemical Aldolizations 170 Conclusions and Outlook 172 CV of Benjamin List 173 Selected Publications 173 Contents XVII Enantioselective Photochemical Reactions 174 Thorsten Bach Background 174 Concept 175 Results 175 Perspectives 176 CV of Thorsten Bach 178 Selected Publications 178 Asymmetric Catalysis via Dynamic Kinetic Resolution 179 Jan -Е. Bäckvall Background 179 Combined Enzyme and Metal Catalysis for Efficient DKR 180 Results 180 Extension to DKR of Amines 182 Conclusions and Future Perspectives 183 CVofJan-E. Bäckvall 183 Selected Publications 183 Catalytic Asymmetric Epoxidation of Enones and Related Compounds 185 Mbrecht Berkessel General 185 Electrophffic Catalytic Epoxidation 186 Nucleophilic Catalytic Epoxidation 186 Conclusions and Future Perspectives 188 CV of Albrecht Berkessel 188 Selected Publications 189 Kinetic Investigations of the Soai Autocatalytic Reaction 190 Donna G. Blackmona Background 190 Kinetic Studies using Reaction Calorimetry 191 CV of Donna G. Blackmond 194 Selected Publications 194 Planar-chiral Heterocycles as Enantioselective Organocatalysts 195 Gregory C. Fu Background and Design 295 Applications 195 Conclusions and Future Perspectives 199 CV of Gregory С Fu 199 Selected Publications 199 XVIII Contents An Organocatalytic Approach to Optically Active Six-membered Rings 200 Karl Anker j0rgensen Background 200 Strategy 201 Results 202 Synthesis of γ- and E-lactones 204 Conclusions and Future Perspectives 204 CV of Karl Anker Jargensen 204 Selected Publications 205 Non-linear Effects in Asymmetric Catalysis 206 Henri B. Kagan Background 206 Enantiomerically Impure Chiral Auxiliaries 206 Non-linear Effects 206 Results 207 Examples of Asymmetric Amplifications 207 Kinetic Models 208 Applications of Non-linear Effects 209 Conclusion and Perspectives 209 CV of Henri B. Kagan 209 Selected Publications 210 Asymmetric Organocatalysis 211 Steven V. Ley Background 223 Results 212 Conclusions and Future Perspectives 216 CV of Steven V. Ley 236 Selected Publications 236 Directed Evolution of Enzymes for Asymmetric Syntheses 237 Manfred T. Reetz Background 217 Strategy and Early Results 237 Generalizing the Concept 239 New Strategies 219 Conclusions and Perspectives 220 CV of Manfred T. Reetz 220 Selected Publications 221 Contents XIX Asymmetrie Autocatalysis and Its Implications in the Origin of Chiral Homogeneity of Biomolecules 222 Kenso Soai and Tsuneomi Kawasaki Background 222 Results 223 Chiral Amplification by Asymmetric Autocatalysis 22i Asymmetric Autocatalysis as a link Between the Origin of Chirality and Highly Enantioenriched Molecules 223 Spontaneous Absolute Asymmetric Synthesis 224 Conclusions and Future Perspectives 226 CV of Kenso Soai 226 CV of Tsuneomi Kawasaki 227 Selected Publications 227 Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase 228 Chi-Huey Wong and William A. Greenberg Background 228 Results 229 Catalytic Mechanism 229 Synthetic Applications 229 Application to the Synthesis of Epothilones and Statins 230 Conclusion 231 CV of Chi-Huey Wong 232 CV of William A. Greenberg 232 Selected Publications 232 Part IV Asymmetric Reactions in Total Synthesis Introductory Chapter 235 К. С Nicolaou and Paul G. Bulger Background 235 Reactions 235 Aldol 235 Alkylation 237 Diels-Alder 239 Allylation 240 Palladium-catalyzed Cross-coupling 241 Epoxidation 244 Dihydroxylation/ammohydroxylation 247 Organocatalytic Reductions 248 Metal-catalyzed Hydrogénations 248 Enzymatic 250 Conclusions 250 CV of К. С Nicolaou 251 CV of Paul G. Bulger 251 Selected Publications 252 XX Contents Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis 254 Nicole Holub and Siegfried Blechert Background and Strategy 254 Results 255 Tetraponerines 255 Tra»s-195A 256 Lasubine II 256 Astrophylline and Dendrochrysine 257 Conclusions and Future Perspectives 25S CV of Siegfried Blechert 259 Selected Publications 259 Asymmetric Synthesis of Biaryls by the Lactone Method 260 Gerhard Bringmann, Tanja Gulder and Tobias A. M. Guider Introduction 260 The Basic Concept of the Lactone Method 260 Application of the Lactone Concept to Natural Product Synthesis 261 Conclusions and Further Perspectives 263 CV of Gerhard Bringmann 263 Selected Publications 264 Asymmetric Synthesis of Merrilactone A 265 Samuel J . Danishefsky Background 265 Synthetic Strategy 265 Synthesis of Merrilactone A 267 CV of Samuel J. Danishefsky 269 Selected Publications 270 Asymmetric Synthesis of Cyclic Ketal and Spiroaminal-containing Natural Products 272 Craig J . Forsyth Background 271 Results 272 Okadaic Acid - Three Spiroketalization Methods 272 Additional Ketals via Double Intramolecular Hetero Michael Additions 273 Synthesis of the Azaspiracid Spiroaminal 274 Conclusion and Future Perspectives 275 CV of Craig J. Forsyth 275 Selected Publications 276 Contents XXI Case Studies at the Metathesis/Asymmetric Synthesis Interface 277 Mois Fürstner Background 277 Results 277 (-(-Gloeosporone 277 (-J-Isooncinotíne 279 Conclusions and Future Perspectives 281 CV of Alois Fürstner 281 Selected Publications 281 Asymmetric Synthesis of Amino Acids by Rhodium and Ruthenium Catalysis 282 Jean Pierre Genet Introduction 282 Asymmetric Hydrogénation Reactions 282 Chiral Diphosphine ligands and Diversity of Chiral Ru Catalysts 283 Results 283 Asymmetric Hydrogénation of Dehydroamino Acids 283 Asymmetric Syntheses of a-Amino ß-Hydroxy Acids (DKR) 284 Asymmetric Syntheses of Natural Products 285 Tandem-1,4 addition/Enantioselective Protonation Catalyzed by Rhodium 285 Conclusions 286 CV of Jean Pierre Genet 286 Selected Publications 287 Asymmetric Syntheses of Pheromones 288 Kenji Mori Background 288 Strategy and Results 288 Derivation from Optically Active Starting Materials 289 Enantiomer Separation 289 Asymmetric Synthesis 290 Conclusion and Future Perspective 292 CV of Kenji Mori 292 Selected Publications 292 Total Synthesis of Polyketides Using Asymmetric Aldol Reactions 293 Ian Paterson Background 293 Results 294 Stereocontrol in the Boron Aldol Reactions of Ketones 294 Application to the Total Synthesis of Altohyrtm A (Spongistatin 1) 296 Conclusions and Future Perspectives 296 CV of Ian Paterson 296 Selected Publications 298 XXII Contents Asymmetrie Synthesis on the Solid Phase 299 Torben Leßmann and Herbert Waldmann Introduction 299 Results 299 Asymmetric Aldol Reactions 299 Asymmetric Cycloadditions 300 Asymmetric Epoxide Openings 302 Other Reactions 302 Conclusion 302 CV of Herbert Waldmann 302 CV of Torben Leßmann 303 Selected Publications 303 Part V Asymmetric Synthesis in Industry Introductory Chapter 307 Herbert Hugl Background 307 Industrial Production of Chiral Compounds 307 Outlook 310 CV of Herbert Hugl 310 Selected Publications 310 Industrial Application of Enantioselective Catalysis 311 Hans-Ulrich Blaser The Potential of Enantioselective Catalysis 311 Hurdles on the Way to an Industrial Process 311 Catalyst Performance 312 Availability and Cost of the Catalyst 312 Development Time 313 Selected Milestones in Industrial Application 333 Conclusions and Future Perspectives 315 CV of Hans-Ulrich Blaser 315 Selected Publications 315 Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant 326 J. Brands, P. Pye and K. Rossen Background 316 Results 317 Bicydic Acetal Approach 317 Lactam Approach 318 Conclusion 320 CV of Karel M. Jos Brands 320 CV of Philip Pye 320 CV of Kai Rossen 320 Selected Publications 321 Contents XXIII Combinatorial Methods in Asymmetric Syntheses 322 Stefan Dahrnen Background 322 Results 322 Ligand Screening 322 Additive Screening 324 Arylzinc Precursors 324 CV of Stefan Dahmen 326 Selected Publications 326 Biocatalytic Production of Optically Active Amines 327 Klaus Ditrich Background 327 Results 327 Conclusions and Future Perspectives 331 CV of Klaus Ditrich 331 Selected Publications 331 The Monsanto L-Dopa Process 332 William S. Knowles Background 332 i-DOPA Process 332 Other Industrial Applications 335 Conclusions 335 CV of William S. Knowles 335 Selected Publications 336 Asymmetric Hydrogénation through Metal-Ligand Bifunctional Catalysis 337 Ryoji Noyori, Takeshi Ohkuma, Christian A. Sandoval and Kilián Muñiz Background 337 Strategy 337 Results 337 Catalytic Cycle 339 CV of Ryoji Noyori 340 Selected Publications 341 XXIV Contents Many Ways are Leading to Rome - Today s Variety of Competing Synthetic Methods in Industry 342 Andreas Job and Andreas Stolle Introduction 342 Synthetic Concepts 343 Biochemical Approach 344 Catalytic Hydrogénation Approach 345 Chiral Pool Synthesis 345 Conclusion 346 CV of Andreas Job 346 CV of Andreas Stolle 346 Selected Publications 347 Author Index 349 Subject Index 352 This Who s who of asymmetric synthesis introduces the reader to the leaders in the field with a four-page concentrate of their area of research along with a short biography. The book is organized into five chapters, each with an introductory preface. Starting from the key concepts of asymmetric synthesis (diastereoselective methods, asym¬ metric catalysis) the focus then shifts to its application to the synthesis natural products and industrial processes Graduate students, academic and industrial researchers will find this book a rich source of inspiration for their own work as well as an indispensable tool for the preparation of seminars and exams. A must for everyone in the field. Mat/lias Christmann was born in Peiné, beated ¡η Lower Saxony, Germany, in 197г, He studied Chemistry in Braunschweig figgj—199SJ and Hannover figgS-sooîj and obtained his doctorate under the guidance of Markus Kalesse. After a postdoctoral appointment with CraigJ. Forsyth at the University of Minnesota (1001-2002), he began his independent research career associated with Dieter Enders at the RWTH Aachen in 200J, His research interests include organocatalysis and natural product synthesis. SUfiin Bräst, born in Kiel, Germany in 1967, studied chemistry in Göttingen, Bangor (UK) and Marseille. He obtained his doctorats ¡η iggj under the guidance of Armin de Meijere in Göttingen. After postdoctoral appoint¬ ments at Uppsala University (Jan Bäckvall) and The Scripps Research Institute (К. C. Nicolaou), he began his independ¬ ent research career at the RWTH Aachen associated with Dieter Enders ¡η 1997 and finished his Habilitation in 3001. He became Professor at the University of Bonn that same year and Full Professor of Organic Chemistry at the Technical University of Karlsruhe m 2003. His research interests include asymmetric metal-catalyzed processes and combinatorial chemistry towards the synthesis of bio¬ logically active compounds.
adam_txt	IX Contents Foreword V Message from the Editors XXV List of Abbreviations XXVII Named and Unnamed Reactions XXXI List of Contributors XXXIII Part I Chiral Auxiliaries in Asymmetric Synthesis Introductory Chapter 3 David A. Evans, Günter Helmchen and Magnus Raping Background 3 Results 4 Summary 7 CV of David A. Evans 8 CV of Günter Helmchen S CV of Magnus Rüping 9 Selected Publications 9 Asymmetric Epoxidation of Pentadienols 10 Reinhard Bruckner Background 10 Objective: Making Building Blocks for the Synthesis of 1,3,5,7,— -Polyols from Epoxyalcohols 11 Results 12 Asymmetric Epoxidation of a Conjugated Pentadienol 12 Asymmetric Epoxidation of a Nonconjugated Pentadienol 13 CV of Reinhard Bruckner IS Selected Publications 16 X Contents Asymmetrie Synthesis using Sulfur-Nitrogen Reagents 17 Franklin A. Davis Background 17 Results 17 Asymmetric Oxidations using N-Sulfonyloxaziridines 17 Asymmetric Fluorination of Enolates with N-Fluoro^lO-Camphorsultams 19 Asymmetric Synthesis of Amine Derivatives using Enantiopure Sulfinimines (N-Sulfinyl Imines) 19 Outlook 20 CV of Franklin A. Davis 20 Selected Publications 22 Asymmetric Syntheses with SAMP^RAMP-Hydrazones 23 Dieter Enders and Wolfgang Bettray Background 23 Strategy 24 Results 25 Application for the Synthesis of Natural Products 26 Other Asymmetric Syntheses from the Enders Group 27 Conclusions and Future Perspectives 27 CV of Dieter Enders 27 Selected Publications 28 Asymmetric Allylation Reactions 29 Reinhard W. Hoffmann Background 29 Results 29 Type (I) Allylmetallation of Aldehydes 29 Second Generation Allylmetallation Reagents 31 CV of Reinhard W. Hoffmann 32 Selected Publications 33 Carbohydrates as Chirai Auxiliaries 34 Horst Kunz Introduction 34 Results 34 Carbohydrate Auxiliaries in Cycloaddition Reactions 34 Conjugate Addition Reactions Directed by Carbohydrate Auxiliaries 35 Glycosylamines in Stereoselective Synthesis 36 Conclusions 38 CV of Horst Kunz 38 Selected Publications 38 Contents XI The Use of Chiral Oxazolines in early C -С Bond Forming Reactions 39 Albert I. Meyers Background 39 Results 40 CV of Albert I. Meyers 41 Selected Publications 41 Asymmetric Synthesis of Amines and Amino Acids from Amines 42 Shun-Ichi Murahashi and Yasushi Imada Background 42 Strategy 43 Results 43 Diastereoselective Reactions of Nitrones 43 Enantioselective Reactions of Nitrones 44 Conclusions and Future Perspectives 46 CV of Shun-Ichi Murahashi 46 Selected Publications 47 Part II Metal-catalyzed Asymmetric Synthesis Introductory Chapter 51 Masakatsu Shibasaki and Shigeki Matsunaga Introduction 51 Design of Asymmetric Metal Catalysis 52 Future Prospects for Metal-catalyzed Asymmetric Synthesis 53 CV of Masakatsu Shibasaki 54 CV of Shigeki Matsunaga 54 Selected Publications 55 Catalytic Asymmetric Sulfur Ylide Mediated Epoxidation of Carbonyl Compounds 56 Varinder Aggarwal Background 56 Results 57 Other Reactions of Sulfur Ylides from the Aggarwal Group 59 Conclusions and Future Perspectives 59 CV of Varinder Aggarwal 60 Selected Publications 61 XII Contents Asymmetrie Baeyer-Villiger Reactions 62 Carsten Bolm Background 62 Strategy 63 Results 64 Other Research Topics from the Bolm Group 65 CV of Carsten Bolm 65 Selected Publications 66 Planar Chiral Ligands Based on p^JParacyclophanes 67 Stefan Bräse Background 67 Strategy 68 Results 69 Application for the Synthesis of Natural Products 70 Other Asymmetric Syntheses from the Bräse Group 70 Conclusions and Future Perspectives 71 CV of Stefan Bräse 71 Selected Publications 71 Asymmetric Syntheses of S-jtrans^-NitrocydopropylJalanine and S-jtrans^-AminocydopropylJalanine 72 Armin de Majere ană Oleg V. Larionov Background 72 Strategy and Results 73 Outlook 75 CV of Armin de Meijere 75 CV of Oleg V Larionov 76 Selected Publications 76 Copper-Bisjoxazoline) Catalyzed Synthesis of ß-Lactams - Enantioseiective Reaction of Alkynes with Nitrones 77 David A. Evans, Florian Kleinbeck and Magnus Rüping Background 77 Results 78 Summary 80 CV of David A. Evans 81 CV of Magnus Rüping 82 CV of Florian Kleinbeck 81 Selected Publications 81 Contents XIII Catalytic Asymmetric Conjugate Addition Reactions of Organometallic Reagents 83 Fernando López and Ben L. Veringa Background 83 The First Catalytic Enantioselective Approaches 83 Results 84 Cu-catalyzed Enantioselective CA of Organozinc Reagents 84 Highly Enantioselective Cu-catalyzed CA of Grignard Reagents 86 Conclusion and Future Perspectives 87 CV of Fernando López 87 CV of Ben L. Feringa 88 Selected Publications 88 Catalytic Asymmetric Synthesis of Allylic Alcohols via Dynamic Kinetic Resolution 90 Hans-Joachim Gais Introduction 90 Strategy 91 Results 91 Application to the Synthesis of Natural Products 94 Other Asymmetric Syntheses from the Gais Group 94 Conclusion and Future Perspectives 94 CV of Hans-Joachim Gais 94 Selected Publications 95 Asymmetric Cross-coupling Reactions 97 Tamio Hayashi Background 97 Results 97 Asymmetric Cross-coupling of Secondary Alkyl Grignard Reagents 97 Asymmetric Cross-Coupling Forming Axially Chiral Biaryls 99 Conclusions and Future Perspectives 100 CV of Tamio Hayashi 101 Selected Publications 101 Asymmetric Allylic Substitutions 102 Günter Heimchen Background 102 Results 103 Pd-Catalyzed Aliylic Substitutions 103 ir-Catalyzed Allylic Substitutions 104 Application for the Synthesis of Biologically Active Compounds 104 Other Asymmetric Syntheses from the Helmchen Group 205 Conclusions and Future Perspectives 105 CV of Günter Helmchen 105 Selected Publications 106 XIV Contents Asymmetrie Homoatdol Reactions 107 Dieter Hoppe Background 107 Results 208 Enantioselective Additions via Stereospecific Deprotonation 108 Enantìoselectìve Additions via (-J-Sparteine-mediated ct-Deprotonations 109 Enantioselective γ -Deprotonations 110 Synthetic Applications 110 CV of Dieter Hoppe 22 2 Selected Publications 222 Asymmetric Vinylogous Mukaiyama Aldol Reaction 222 Markus Katesse and Jorma Hassfeld Introduction 222 Results 112 Conclusions and Further Perspectives 225 CV of Markus Kaiesse 116 CV of Jorma Hassfeld 2 2 б Selected Publications 226 Chiral Lewis Acid Catalysis in Aqueous Media 117 Shu Kobayashi and Chikako Ogawa Background 227 Results 117 Water-compatible Lewis Acid 227 Asymmetric Aldol Reactions 228 Asymmetric Hydroxymethylatkm Reactions 229 Asymmetric Mannich-type Reactions 220 CV of Shu Kobayashi 222 CV of Chikako Ogawa 222 Selected Publications 222 Asymmetric Epoxidation of Non-activated Olefins 123 Kazuhiro Matsumoto and Tsutomu Katsuki Introduction 223 Results 223 Manganese(salen) Catalyst 223 Ruthenium(salen) Catalyst 224 Titanium(salalen) Catalyst 225 Conclusion 126 CV of Tsutomu Katsuki 227 CV of Kazuhiro Matsumoto 127 Selected Publications 227 Contents XV Chiral Carbonyl Lewis Acid Complexes in Asymmetrie Syntheses 128 Keiji Maruoka and Takashi Ooi Background 128 Results 128 Conclusions and Future Perspectives 131 CV of Keiji Maruoka 131 CV of Takashi Ooi 131 Selected Publications 132 ZACA Reaction: Zr-catalyzed Asymmetric Carboalumination of Alkenes 133 Ei-ichi Negishi, Bo Liang, Tibor Novak and Ze Tan Background and Discovery 133 Results 134 ZACA-Pd-catalyzed Cross-coupling Tandem Processes for the Synthesis of Deoxypolypropionates and Related Compounds 134 Synthesis of 2 -Methyl- or 2-Eťhyl-l-alkanols Not Readily Purifiable by Chromatography or Recrystallization 137 CV of Ei-ichi Negishi 137 Selected Publications 138 Bisoxazolines - a Privileged Ligand Class for Asymmetric Catalysis 139 Andreas Pfaltz Background 139 Results 140 Semicorrins 140 C2 -Symmetric Bisoxazolines 140 Boron-bridged Bisoxazolines 142 Conclusion 142 CV of Andreas Pfaltz 142 Selected Publications 143 Enantioselective Cycloaddition Reactions Catalyzed by Hydrogen Bonding 144 Viresh H. Rawal and Avinash N. Thadani Background 144 Strategy 146 Results 146 Application to Other Reactions 147 Conclusions and Future Perspectives 147 CV of Viresh H. Rawal 147 Selected Publications 148 XVI Contents Direct Catalytic Asymmetric Aldol-Tishchenko Reaction 149 Masakatsu Shibasaki and Takashi Ohshima Background 349 Strategy 150 Results 150 Mechanistic Studies 152 Conclusions and Future Perspectives 253 CV of Masakatsu Shibasaki 153 CV of Takashi Ohshima 153 Selected Publications 154 Asymmetric Heck and other Palladium-catalyzed Reactions 155 Lutz F. Tietze and Florian Lotz Background 155 Enantioselective Heck Reactions with Allylsilanes as the Alkene Component 155 CV of Lutz F. Tietze 159 CV of Florian Lotz 159 Selected Publications 160 Asymmetric Catalysis with Chiral Acid 162 Hisashi Yamamoto Background 161 Results 162 C2 Symmetric Chiral Lewis Acid Catalysts 162 Combined Acid Catalyst 162 CV of Hisashi Yamamoto 165 Selected Publications 165 Part III Biocatalysis and Organocatalysis: Asymmetric Synthesis Inspired by Nature Introductory Chapter 169 Benjamin List Introduction 169 The Aldol Reaction as an Example 269 Asymmetric Chemical Aldolizations 170 Conclusions and Outlook 172 CV of Benjamin List 173 Selected Publications 173 Contents XVII Enantioselective Photochemical Reactions 174 Thorsten Bach Background 174 Concept 175 Results 175 Perspectives 176 CV of Thorsten Bach 178 Selected Publications 178 Asymmetric Catalysis via Dynamic Kinetic Resolution 179 Jan -Е. Bäckvall Background 179 Combined Enzyme and Metal Catalysis for Efficient DKR 180 Results 180 Extension to DKR of Amines 182 Conclusions and Future Perspectives 183 CVofJan-E. Bäckvall 183 Selected Publications 183 Catalytic Asymmetric Epoxidation of Enones and Related Compounds 185 Mbrecht Berkessel General 185 Electrophffic Catalytic Epoxidation 186 Nucleophilic Catalytic Epoxidation 186 Conclusions and Future Perspectives 188 CV of Albrecht Berkessel 188 Selected Publications 189 Kinetic Investigations of the Soai Autocatalytic Reaction 190 Donna G. Blackmona Background 190 Kinetic Studies using Reaction Calorimetry 191 CV of Donna G. Blackmond 194 Selected Publications 194 Planar-chiral Heterocycles as Enantioselective Organocatalysts 195 Gregory C. Fu Background and Design 295 Applications 195 Conclusions and Future Perspectives 199 CV of Gregory С Fu 199 Selected Publications 199 XVIII Contents An Organocatalytic Approach to Optically Active Six-membered Rings 200 Karl Anker j0rgensen Background 200 Strategy 201 Results 202 Synthesis of γ- and E-lactones 204 Conclusions and Future Perspectives 204 CV of Karl Anker Jargensen 204 Selected Publications 205 Non-linear Effects in Asymmetric Catalysis 206 Henri B. Kagan Background 206 Enantiomerically Impure Chiral Auxiliaries 206 Non-linear Effects 206 Results 207 Examples of Asymmetric Amplifications 207 Kinetic Models 208 Applications of Non-linear Effects 209 Conclusion and Perspectives 209 CV of Henri B. Kagan 209 Selected Publications 210 Asymmetric Organocatalysis 211 Steven V. Ley Background 223 Results 212 Conclusions and Future Perspectives 216 CV of Steven V. Ley 236 Selected Publications 236 Directed Evolution of Enzymes for Asymmetric Syntheses 237 Manfred T. Reetz Background 217 Strategy and Early Results 237 Generalizing the Concept 239 New Strategies 219 Conclusions and Perspectives 220 CV of Manfred T. Reetz 220 Selected Publications 221 Contents XIX Asymmetrie Autocatalysis and Its Implications in the Origin of Chiral Homogeneity of Biomolecules 222 Kenso Soai and Tsuneomi Kawasaki Background 222 Results 223 Chiral Amplification by Asymmetric Autocatalysis 22i Asymmetric Autocatalysis as a link Between the Origin of Chirality and Highly Enantioenriched Molecules 223 Spontaneous Absolute Asymmetric Synthesis 224 Conclusions and Future Perspectives 226 CV of Kenso Soai 226 CV of Tsuneomi Kawasaki 227 Selected Publications 227 Asymmetric Synthesis using Deoxyribose-5-phosphate Aldolase 228 Chi-Huey Wong and William A. Greenberg Background 228 Results 229 Catalytic Mechanism 229 Synthetic Applications 229 Application to the Synthesis of Epothilones and Statins 230 Conclusion 231 CV of Chi-Huey Wong 232 CV of William A. Greenberg 232 Selected Publications 232 Part IV Asymmetric Reactions in Total Synthesis Introductory Chapter 235 К. С Nicolaou and Paul G. Bulger Background 235 Reactions 235 Aldol 235 Alkylation 237 Diels-Alder 239 Allylation 240 Palladium-catalyzed Cross-coupling 241 Epoxidation 244 Dihydroxylation/ammohydroxylation 247 Organocatalytic Reductions 248 Metal-catalyzed Hydrogénations 248 Enzymatic 250 Conclusions 250 CV of К. С Nicolaou 251 CV of Paul G. Bulger 251 Selected Publications 252 XX Contents Ring Rearrangement Metathesis (RRM) in Alkaloid Synthesis 254 Nicole Holub and Siegfried Blechert Background and Strategy 254 Results 255 Tetraponerines 255 Tra»s-195A 256 Lasubine II 256 Astrophylline and Dendrochrysine 257 Conclusions and Future Perspectives 25S CV of Siegfried Blechert 259 Selected Publications 259 Asymmetric Synthesis of Biaryls by the 'Lactone Method' 260 Gerhard Bringmann, Tanja Gulder and Tobias A. M. Guider Introduction 260 The Basic Concept of the 'Lactone Method' 260 Application of the 'Lactone Concept to Natural Product Synthesis 261 Conclusions and Further Perspectives 263 CV of Gerhard Bringmann 263 Selected Publications 264 Asymmetric Synthesis of Merrilactone A 265 Samuel J . Danishefsky Background 265 Synthetic Strategy 265 Synthesis of Merrilactone A 267 CV of Samuel J. Danishefsky 269 Selected Publications 270 Asymmetric Synthesis of Cyclic Ketal and Spiroaminal-containing Natural Products 272 Craig J . Forsyth Background 271 Results 272 Okadaic Acid - Three Spiroketalization Methods 272 Additional Ketals via Double Intramolecular Hetero Michael Additions 273 Synthesis of the Azaspiracid Spiroaminal 274 Conclusion and Future Perspectives 275 CV of Craig J. Forsyth 275 Selected Publications 276 Contents XXI Case Studies at the Metathesis/Asymmetric Synthesis Interface 277 Mois Fürstner Background 277 Results 277 (-(-Gloeosporone 277 (-J-Isooncinotíne 279 Conclusions and Future Perspectives 281 CV of Alois Fürstner 281 Selected Publications 281 Asymmetric Synthesis of Amino Acids by Rhodium and Ruthenium Catalysis 282 Jean Pierre Genet Introduction 282 Asymmetric Hydrogénation Reactions 282 Chiral Diphosphine ligands and Diversity of Chiral Ru Catalysts 283 Results 283 Asymmetric Hydrogénation of Dehydroamino Acids 283 Asymmetric Syntheses of a-Amino ß-Hydroxy Acids (DKR) 284 Asymmetric Syntheses of Natural Products 285 Tandem-1,4 addition/Enantioselective Protonation Catalyzed by Rhodium 285 Conclusions 286 CV of Jean Pierre Genet 286 Selected Publications 287 Asymmetric Syntheses of Pheromones 288 Kenji Mori Background 288 Strategy and Results 288 Derivation from Optically Active Starting Materials 289 Enantiomer Separation 289 Asymmetric Synthesis 290 Conclusion and Future Perspective 292 CV of Kenji Mori 292 Selected Publications 292 Total Synthesis of Polyketides Using Asymmetric Aldol Reactions 293 Ian Paterson Background 293 Results 294 Stereocontrol in the Boron Aldol Reactions of Ketones 294 Application to the Total Synthesis of Altohyrtm A (Spongistatin 1) 296 Conclusions and Future Perspectives 296 CV of Ian Paterson 296 Selected Publications 298 XXII Contents Asymmetrie Synthesis on the Solid Phase 299 Torben Leßmann and Herbert Waldmann Introduction 299 Results 299 Asymmetric Aldol Reactions 299 Asymmetric Cycloadditions 300 Asymmetric Epoxide Openings 302 Other Reactions 302 Conclusion 302 CV of Herbert Waldmann 302 CV of Torben Leßmann 303 Selected Publications 303 Part V Asymmetric Synthesis in Industry Introductory Chapter 307 Herbert Hugl Background 307 Industrial Production of Chiral Compounds 307 Outlook 310 CV of Herbert Hugl 310 Selected Publications 310 Industrial Application of Enantioselective Catalysis 311 Hans-Ulrich Blaser The Potential of Enantioselective Catalysis 311 Hurdles on the Way to an Industrial Process 311 Catalyst Performance 312 Availability and Cost of the Catalyst 312 Development Time 313 Selected Milestones in Industrial Application 333 Conclusions and Future Perspectives 315 CV of Hans-Ulrich Blaser 315 Selected Publications 315 Crystallization-Induced Diastereoselection for the Synthesis of Aprepitant 326 J. Brands, P. Pye and K. Rossen Background 316 Results 317 Bicydic Acetal Approach 317 Lactam Approach 318 Conclusion 320 CV of Karel M. Jos Brands 320 CV of Philip Pye 320 CV of Kai Rossen 320 Selected Publications 321 Contents XXIII Combinatorial Methods in Asymmetric Syntheses 322 Stefan Dahrnen Background 322 Results 322 Ligand Screening 322 Additive Screening 324 Arylzinc Precursors 324 CV of Stefan Dahmen 326 Selected Publications 326 Biocatalytic Production of Optically Active Amines 327 Klaus Ditrich Background 327 Results 327 Conclusions and Future Perspectives 331 CV of Klaus Ditrich 331 Selected Publications 331 The Monsanto L-Dopa Process 332 William S. Knowles Background 332 i-DOPA Process 332 Other Industrial Applications 335 Conclusions 335 CV of William S. Knowles 335 Selected Publications 336 Asymmetric Hydrogénation through Metal-Ligand Bifunctional Catalysis 337 Ryoji Noyori, Takeshi Ohkuma, Christian A. Sandoval and Kilián Muñiz Background 337 Strategy 337 Results 337 Catalytic Cycle 339 CV of Ryoji Noyori 340 Selected Publications 341 XXIV Contents Many Ways are Leading to Rome - Today's Variety of Competing Synthetic Methods in Industry 342 Andreas Job and Andreas Stolle Introduction 342 Synthetic Concepts 343 Biochemical Approach 344 Catalytic Hydrogénation Approach 345 Chiral Pool Synthesis 345 Conclusion 346 CV of Andreas Job 346 CV of Andreas Stolle 346 Selected Publications 347 Author Index 349 Subject Index 352 This "Who's who" of asymmetric synthesis introduces the reader to the leaders in the field with a four-page concentrate of their area of research along with a short biography. The book is organized into five chapters, each with an introductory preface. Starting from the key concepts of asymmetric synthesis (diastereoselective methods, asym¬ metric catalysis) the focus then shifts to its application to the synthesis natural products and industrial processes Graduate students, academic and industrial researchers will find this book a rich source of inspiration for their own work as well as an indispensable tool for the preparation of seminars and exams. A must for everyone in the field. Mat/lias Christmann was born in Peiné, beated ¡η Lower Saxony, Germany, in 197г, He studied Chemistry in Braunschweig figgj—199SJ and Hannover figgS-sooîj and obtained his doctorate under the guidance of Markus Kalesse. After a postdoctoral appointment with CraigJ. Forsyth at the University of Minnesota (1001-2002), he began his independent research career associated with Dieter Enders at the RWTH Aachen in 200J, His research interests include organocatalysis and natural product synthesis. SUfiin Bräst, born in Kiel, Germany in 1967, studied chemistry in Göttingen, Bangor (UK) and Marseille. He obtained his doctorats ¡η iggj under the guidance of Armin de Meijere in Göttingen. After postdoctoral appoint¬ ments at Uppsala University (Jan Bäckvall) and The Scripps Research Institute (К. C. Nicolaou), he began his independ¬ ent research career at the RWTH Aachen associated with Dieter Enders ¡η 1997 and finished his "Habilitation" in 3001. He became Professor at the University of Bonn that same year and Full Professor of Organic Chemistry at the Technical University of Karlsruhe m 2003. His research interests include asymmetric metal-catalyzed processes and combinatorial chemistry towards the synthesis of bio¬ logically active compounds.
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spelling	Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse 2., completely rev. ed. Weinheim WILEY-VCH 2008 XL, 355 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Asymmetrische Synthese (DE-588)4135603-2 s DE-604 Christmann, Mathias 1972- Sonstige (DE-588)122971035 oth Bräse, Stefan Sonstige oth http://deposit.dnb.de/cgi-bin/dokserv?id=2774561&prov=M&dok_var=1&dok_ext=htm Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis Digitalisierung UB Regensburg application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=016226644&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Klappentext
spellingShingle	Asymmetric synthesis the essentials Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd
subject_GND	(DE-588)4135603-2 (DE-588)4143413-4
title	Asymmetric synthesis the essentials
title_auth	Asymmetric synthesis the essentials
title_exact_search	Asymmetric synthesis the essentials
title_exact_search_txtP	Asymmetric synthesis the essentials
title_full	Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse
title_fullStr	Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse
title_full_unstemmed	Asymmetric synthesis the essentials ed. by Mathias Christmann and Stefan Bräse
title_short	Asymmetric synthesis
title_sort	asymmetric synthesis the essentials
title_sub	the essentials
topic	Chiraliteit gtt Enantiomeren gtt Stereochemie gtt Stereoselectiviteit gtt Synthese (chemie) gtt Asymmetric synthesis Asymmetrische Synthese (DE-588)4135603-2 gnd
topic_facet	Chiraliteit Enantiomeren Stereochemie Stereoselectiviteit Synthese (chemie) Asymmetric synthesis Asymmetrische Synthese Aufsatzsammlung
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