Modern Organic Synthesis - An Introduction

Informationen zum Autor GEORGE S. ZWEIFEL, PhD, is Professor Emeritus at the University of California, Davis.MICHAEL H. NANTZ, PhD, is Professor of Chemistry and Distinguished University Scholar at the University of Louisville.PETER SOMFAI, PhD, is Professor of Chemistry at Lund University. Klappentext Organized into 10 chapters, Modern Organic Synthesis covers key concepts that include retrosynthesis, conformational analysis, and functional group transformations as well as presents the latest developments in organometallic chemistry and C-C bond formation. The new edition thoroughly updates the material, examples, and literature references.Continuing the legacy of its innovative predecessor, this second edition is designed for senior undergraduate and beginning graduate students to provide them with a necessary background to begin research in either an industry or academic environment.The authors, all of whom are experienced researchers in organic chemistry, have selected and present the modern techniques and methods likely to be encountered in a synthetic project - with examples based on applicability, versatility, and selectivity. Zusammenfassung This book bridges the gap between sophomore and advanced / graduate level organic chemistry courses, providing students with a necessary background to begin research in either an industry or academic environment. Inhaltsverzeichnis About the Authors ixPreface to the Second Edition xiPreface to the First Edition xiiiSyntheticDesign 11.1 Retrosynthetic Analysis 11.2 Reversal of the Carbonyl Group Polarity (Umpolung) 61.3 Steps in Planning a Synthesis 111.4 Choice of SyntheticMethod 161.5 Domino Reactions (Cascade or Tandem Reactions) 181.6 Computer-Assisted Retrosynthetic Analysis 19References 19Stereochemical Considerations in Planning Syntheses 212.1 Conformational Analysis 212.2 Evaluation of Non-Bonded Interactions 252.3 Six-Membered Heterocyclic Systems 292.4 Polycyclic Ring Systems 302.5 Cyclohexyl Systems with sp2-Hybridized Atoms 332.6 Significant Energy Difference 352.7 Computer-Assisted Molecular Modeling 352.8 Reactivity and Product Determination as a Function of Conformation 36References 42The Concept of Protecting Functional Groups 453.1 Protection of N-H Groups 453.2 Protection of OH Groups 483.3 Protection of Diols as Acetals 553.4 Protection of Carbonyl Groups in Aldehydes and Ketones 563.5 Protection of the Carboxyl Group 623.6 Protection of Double Bonds 663.7 Protection of Triple Bonds 66References 66Functional Group Transformations 714.1 Oxidation of Alcohols to Aldehydes and Ketones 714.2 Reagents and Procedures for Alcohol Oxidation 724.3 Chemoselective Oxidizing Agents 764.4 Oxidation of Acyloins 794.5 Oxidation of Tertiary Allylic Alcohols 794.6 Oxidative Procedures to Carboxylic Acids 804.7 Allylic Oxidation of Alkenes 824.8 Terminology for Reduction of Carbonyl Compounds 854.9 Nucleophilic Reducing Agents 864.10 Electrophilic Reducing Agents 914.11 Regio- and Chemoselective Reductions 934.12 Diastereoselective Reductions of Cyclic Ketones 974.13 Inversion of Secondary Alcohol Stereochemistry 984.14 Diastereofacial Selectivity in Acyclic Systems 994.15 Enantioselective Reductions 104References 108Functional Group Transformations 1155.1 Reactions of Carbon-Carbon Double Bonds 1155.2 Reactions of Carbon-Carbon Triple Bonds 160References 167Formation of Carbon-Carbon Single Bonds via Enolate Anions 1756.1 1,3-Dicarbonyl Compounds 1756.2 Direct Alkylation of Enolates 1856.3 Cyclization Reactions--Baldwin's Rules for Ring Closure 1936.4 Stereochemistry of Cyclic Ketone Alkylation 1956.5 Imine and Hydrazone Anions 1966.6 Enamines 1976.7 The Aldol Reaction 1996.8 Condensation Reactions of Enols and Enolates 2136.9 Robinson Annulation 217References 220Formation of Carbon-Carbon Bonds via Organometal...

List of contents

About the Authors ix
 
Preface to the Second Edition xi
 
Preface to the First Edition xiii
 
SyntheticDesign 1
 
1.1 Retrosynthetic Analysis 1
 
1.2 Reversal of the Carbonyl Group Polarity (Umpolung) 6
 
1.3 Steps in Planning a Synthesis 11
 
1.4 Choice of SyntheticMethod 16
 
1.5 Domino Reactions (Cascade or Tandem Reactions) 18
 
1.6 Computer-Assisted Retrosynthetic Analysis 19
 
References 19
 
Stereochemical Considerations in Planning Syntheses 21
 
2.1 Conformational Analysis 21
 
2.2 Evaluation of Non-Bonded Interactions 25
 
2.3 Six-Membered Heterocyclic Systems 29
 
2.4 Polycyclic Ring Systems 30
 
2.5 Cyclohexyl Systems with sp2-Hybridized Atoms 33
 
2.6 Significant Energy Difference 35
 
2.7 Computer-Assisted Molecular Modeling 35
 
2.8 Reactivity and Product Determination as a Function of Conformation 36
 
References 42
 
The Concept of Protecting Functional Groups 45
 
3.1 Protection of N-H Groups 45
 
3.2 Protection of OH Groups 48
 
3.3 Protection of Diols as Acetals 55
 
3.4 Protection of Carbonyl Groups in Aldehydes and Ketones 56
 
3.5 Protection of the Carboxyl Group 62
 
3.6 Protection of Double Bonds 66
 
3.7 Protection of Triple Bonds 66
 
References 66
 
Functional Group Transformations 71
 
4.1 Oxidation of Alcohols to Aldehydes and Ketones 71
 
4.2 Reagents and Procedures for Alcohol Oxidation 72
 
4.3 Chemoselective Oxidizing Agents 76
 
4.4 Oxidation of Acyloins 79
 
4.5 Oxidation of Tertiary Allylic Alcohols 79
 
4.6 Oxidative Procedures to Carboxylic Acids 80
 
4.7 Allylic Oxidation of Alkenes 82
 
4.8 Terminology for Reduction of Carbonyl Compounds 85
 
4.9 Nucleophilic Reducing Agents 86
 
4.10 Electrophilic Reducing Agents 91
 
4.11 Regio- and Chemoselective Reductions 93
 
4.12 Diastereoselective Reductions of Cyclic Ketones 97
 
4.13 Inversion of Secondary Alcohol Stereochemistry 98
 
4.14 Diastereofacial Selectivity in Acyclic Systems 99
 
4.15 Enantioselective Reductions 104
 
References 108
 
Functional Group Transformations 115
 
5.1 Reactions of Carbon-Carbon Double Bonds 115
 
5.2 Reactions of Carbon-Carbon Triple Bonds 160
 
References 167
 
Formation of Carbon-Carbon Single Bonds via Enolate Anions 175
 
6.1 1,3-Dicarbonyl Compounds 175
 
6.2 Direct Alkylation of Enolates 185
 
6.3 Cyclization Reactions--Baldwin's Rules for Ring Closure 193
 
6.4 Stereochemistry of Cyclic Ketone Alkylation 195
 
6.5 Imine and Hydrazone Anions 196
 
6.6 Enamines 197
 
6.7 The Aldol Reaction 199
 
6.8 Condensation Reactions of Enols and Enolates 213
 
6.9 Robinson Annulation 217
 
References 220
 
Formation of Carbon-Carbon Bonds via Organometallic Reagents 227
 
7.1 Organolithium Reagents 227
 
7.2 Organomagnesium Reagents 236
 
7.3 Organotitanium Reagents 239
 
7.4 Organocerium Reagents 240
 
7.5 Organocopper Reagents 241
 
7.6 Organochromium Reagents 251
 
7.7 Organozinc Reagents 252
 
7.8 Organoboron Reagents 256
 
7.9 Organosilicon Reagents 264
 
7.10 Organogold Chemistry 274
 
References 278
 
Palladium-Catalyzed Coupling Reactions 285
 
8.1 Palladium Oxidation State 285
 
8.2 Organic Synthesis with Palladium(0) Complexes 286
 
8.3 The Heck Reaction--Palladium(0)-Cata

Product details

• Authors: Michael Nantz, Michael H Nantz, Michael H. Nantz, Michael H. Zweifel Nantz, Nantz Michael H., Peter Somfai, Somfai Peter, Zweifel, George Zweifel, George S Zweifel, George S. Zweifel, George S. Nantz Zweifel, Gs Zweifel, Zweifel George S.
• Publisher: Wiley, John and Sons Ltd
• Languages: English
• Product format: Paperback / Softback
• Released: 31.05.2016
• EAN: 9781119086536
• ISBN: 978-1-119-08653-6
• No. of pages: 416
• Subjects: Natural sciences, medicine, IT, technology > Chemistry > Organic chemistry; Chemie, Organische Chemie, ORGANIC CHEMISTRY, chemistry, Organische Synthese, Pharmaceutical & Medicinal Chemistry, Pharmazeutische u. Medizinische Chemie, Allg. Chemie