Molecular Rearrangements in Organic Synthesis

Informationen zum Autor Christian M. Rojas, PhD, is Professor of Chemistry at Barnard College. He obtained his Ph.D. at Indiana University in 1995 and did postdoctoral studies at the Massachusetts Institute of Technology and then at The Scripps Research Institute. Professor Rojas began his independent career at Barnard College in 1997. His research explores the use of acyl nitrenes for the synthesis of amino sugars. Klappentext Designed for practitioners of organic synthesis, this book helps chemists understand and take advantage of rearrangement reactions to enhance the synthesis of useful chemical compounds.* Provides ready access to the genesis, mechanisms, and synthetic utility of rearrangement reactions* Emphasizes strategic synthetic planning and implementation* Covers 20 different rearrangement reactions* Includes applications for synthesizing compounds useful as natural products, medicinal compounds, functional materials, and physical organic chemistry Zusammenfassung Designed for practitioners of organic synthesis, this book helps chemists understand and take advantage of rearrangement reactions to enhance the synthesis of useful chemical compounds.* Provides ready access to the genesis, mechanisms, and synthetic utility of rearrangement reactions* Emphasizes strategic synthetic planning and implementation* Covers 20 different rearrangement reactions* Includes applications for synthesizing compounds useful as natural products, medicinal compounds, functional materials, and physical organic chemistry Inhaltsverzeichnis LIST OF CONTRIBUTORS xvii PREFACE xxi PART 1 1,2-MIGRATIONS 1 1 Pinacol and Semipinacol Rearrangements in Total Synthesis 3 1.1 Introduction 3 1.2 Pinacol Reaction 4 1.3 Semipinacol Rearrangement 15 1.4 Conclusion 30 References 32 2 Baeyer-Villiger (BV) Oxidation/Rearrangement in Organic Synthesis 35 2.1 Introduction 35 2.2 Mechanism 35 2.3 Synthetic Applications 37 2.4 Summary and Outlook 55 References 55 3 The Wolff Rearrangement: Tactics, Strategies and Recent Applications in Organic Synthesis 59 3.1 Introduction 59 3.2 Tactics and Strategies via the Wolff Rearrangement 60 3.3 Mechanistic Features and Selectivity Issues of the Wolff Rearrangement 63 3.4 Preparation of ¿-Diazocarbonyl Compounds 64 3.5 Recent Synthetic Applications of the Wolff Rearrangement 67 3.6 Conclusion and Outlook 80 References 81 4 Alkyl and Acyl Azide Rearrangements 85 4.1 Introduction 85 4.2 Alkyl Azide Rearrangements 86 4.3 Acyl Azide Rearrangements 98 4.4 Hofmann Rearrangement 102 4.5 Lossen Rearrangement 104 4.6 Conclusion 107 References 108 5 Beckmann Rearrangements and Fragmentations in Organic Synthesis 111 5.1 Introduction 111 5.2 Strategic Planning: A Historical Perspective 118 5.3 Recent Applications Toward the Synthesis of Natural Products 121 5.4 Access to Diverse Scaffolds via the Beckmann Reaction 129 5.4.1 Diterpene Hydrocarbons 129 5.5 Formation of Heterocyclic Scaffolds 136 5.6 Synthesis of Functional Groups 140 5.7 Summary and Outlook 144 References 145 6 Brook Rearrangement 151 6.1 Introduction 151 6.2 Mechanism 152 6.3 Methods for Generation of ¿-Silyl Alkoxides 153 6.4 Synthetic Reactions Using Brook Rearrangements in the Reactions of Acylsilanes with Nucleophiles 154 6.5 Synthetic Reactions Using Brook Rearrangements Triggered by Deprotonation of ¿-Silyl Alcohols 166 6.6 Synthetic Reactions Using Brook Rearrangements Triggered by Addition of Silylmetallic Reagents 169 6.7 Synthetic Reactions Using Brook Rearrangements in ß-Silyl Alkoxides Generated via Regioselective

Dettagli sul prodotto

• Autori: Rojas, Christian M Rojas, Christian M. Rojas, CM Rojas
• Editore: Wiley, John and Sons Ltd
• Lingue: Inglese
• Formato: Copertina rigida
• Pubblicazione: 04.12.2015
• EAN: 9781118347966
• ISBN: 978-1-118-34796-6
• Pagine: 776
• Categoria: Scienze naturali, medicina, informatica, tecnica > Chimica > Chimica organica