Modern Organic Synthesis

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

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.