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: synthesis of aziridines; nucleophilic ring-opening of aziridines and epoxides; organic synthesis with aziridine building blocks; vinyl aziridines in organic synthesis; diastereoselective aziridination reagents; synthetic aspects of aziridinomitocene chemistry; biosynthesis of biologically important aziridines; organic catalysis of epoxide and aziridine ring formation; metal-mediated synthesis of epoxides; asymmetric epoxide ring opening chemistry; epoxides in complex molecule synthesis; and, biological activity of epoxide-containing molecules. It is a high-quality reference manual for academic and industrial chemists alike.
Professor Andrei K. Yudin obtained his PhD degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah. He then took up a post-doctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. His research interests are in transition metal catalysis, development of novel synthetic methods, and synthesis of complex heterocycles of biological significance.
Foreword. Preface. List of Contributors. 1 Asymmetric Synthesis of Epoxides and Aziridines from Aldehydes and Imines (Varinder K. Aggarwal, D. Michael Badine, and Vijayalakshmi A. Moorthie). 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 . 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 (Ping Zhou, Bang-Chi Chen, and Franklin A. Davis). 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 (Dedicated, with respect, to Professor Sir Charles Rees, FRS Joseph B. Sweeney). 4.1 Introduction. 4.2 Overview and General Features. 4.3 Conclusions. References. 5 Metalated Epoxides and Aziridines in Synthesis (David M. Hodgson and Christopher D. Bray). 5.1 Introduction. 5.2 Metalated Epoxides. 5.3 Metalated Aziridines. 5.4 Outlook. References. 6 Metal-catalyzed Synthesis of Epoxides (Hans Adolfsson and Daniela Balan). 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 (Lars P. C. Nielsen and Eric N. Jacobsen). 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 (Paolo Crotti and Mauro Pineschi). 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 (Berit Olofsson and Peter Somfai). 9.1 Synthesis of Vinylepoxides. 9.2 Transformations of Vinylepoxides. 9.3 Conclusions. References. 10 The Biosynthesis of Epoxides (Sabine Gruschow and David H. Sherman). 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 (Philip A. S. Lowden). 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 (Valery V. Fokin and Peng Wu). 12.1 Introduction. 12.2 Epoxides in Click Chemistry. 12.3 Aziridines in Click Chemistry. 12.4 Aziridinium Ions in Click Chemistry. References. Index.