Z705667
Sigma
Aziridines and Epoxides in Organic Synthesis
| ISBN-10: | 3-527-31213-7 |
| ISBN-13: | 978-3-527-31213-9 |
Description
| General description | Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons. Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings. Filling a gap in the literature, this clearly structured book presents the much needed information in a compact and concise way. The renowned editor has succeeded in gathering together excellent authors to cover synthesis, applications, and the biological aspects in equal depth. Divided roughly equally between aziridines and epoxides, the twelve chapters discuss a variety of topics of interest to chemists. |
Properties
| publication info | A. Yudin, John Wiley & Sons, 2006, 516 pp., hard cover |
Table Of Contents
| Table of Contents | 1 Asymmetric Synthesis of Epoxides and Aziridines from Aldehydes and Imines 1.1 Introduction. 1.2 Asymmetric Epoxidation of Carbonyl Compounds. 1.3 Asymmetric Aziridination of Imines. 1.4 Summary and Outlook. References. 2 Vinylaziridines in Organic Synthesis (Hiroaki Ohno). 2.1 Introduction. 2.2 Direct Synthesis of Vinylaziridines [1]. 2.3 Ring-opening Reactions with Nucleophiles. 2.4 Isomerization Including Rearrangement. 2.5 Cycloaddition. 2.6 Electron Transfer to Vinylaziridines. 2.7 Conclusions. References. 3 Asymmetric Syntheses with Aziridinecarboxylate and Aziridinephosphonate Building Blocks 3.1 Introduction. 3.2 Preparation of Aziridine-2-carboxylates and Aziridine-2-phosphonates. 3.3 Reactions of Aziridine-2-carboxylates and Aziridine-2-phosphonates. 3.4 Applications in Natural Product Syntheses. 3.5 Summary and Conclusions. References. 4 Synthesis of Aziridines 4.1 Introduction. 4.2 Overview and General Features. 4.3 Conclusions. References. 5 Metalated Epoxides and Aziridines in Synthesis 5.1 Introduction. 5.2 Metalated Epoxides. 5.3 Metalated Aziridines. 5.4 Outlook. References. 6 Metal-catalyzed Synthesis of Epoxides 6.1 Introduction. 6.2 Oxidants Available for Selective Transition Metal-catalyzed Epoxidation. 6.3 Epoxidations of Olefins Catalyzed by Early Transition Metals. 6.4 Chromium-, Molybdenum-, and Tungsten-catalyzed Epoxidations. 6.5 Manganese-catalyzed Epoxidations. 6.6 Rhenium-catalyzed Epoxidations. 6.7 Iron-catalyzed Epoxidations. 6.8 Ruthenium-catalyzed Epoxidations. 6.9 Concluding Remarks. References. 7 Catalytic Asymmetric Epoxide Ring-opening Chemistry 7.1 Introduction. 7.2 Enantioselective Nucleophilic Addition to Meso-Epoxides. 7.3 Kinetic Resolution of Racemic Epoxides. 7.4 Enantioselective Rearrangements of Epoxides. 7.5 Conclusion. References. 8 Epoxides in Complex Molecule Synthesis 8.1 Introduction. 8.2 Synthesis of Complex Molecules by Intramolecular Ring-opening of Epoxides with Heteronucleophiles. 8.3 Synthesis of Complex Molecules by Ring-opening of Epoxides with C-Nucleophiles. 8.4 Epoxy Glycals. 8.5 Synthesis of Complex Molecules by Rearrangement Reactions of Epoxides. References. 9 Vinylepoxides in Organic Synthesis 9.1 Synthesis of Vinylepoxides. 9.2 Transformations of Vinylepoxides. 9.3 Conclusions. References. 10 The Biosynthesis of Epoxides 10.1 Introduction. 10.2 Cytochrome P450 Monooxygenases. 10.3 Flavin-dependent Epoxidases. 10.4 Dioxygenases. 10.5 Epoxidation through Dehydrogenation. 10.6 Dehalogenases. 10.7 Summary and Outlook. References. 11 Aziridine Natural Products – Discovery, Biological Activity and Biosynthesis 11.1 Introduction and Overview. 11.2 Mitomycins and Related Natural Products. 11.3 The Azinomycins. 11.4 Other Aziridine Natural Products. References. 12 Epoxides and Aziridines in Click Chemistry 12.1 Introduction. 12.2 Epoxides in Click Chemistry. 12.3 Aziridines in Click Chemistry. 12.4 Aziridinium Ions in Click Chemistry. References. Index. |
