Phosphines as Reagents and Catalysts in Organic Synthesis provides comprehensive coverage of metal-free organic reactions with phosphines as reagents or catalysts, as well as their synthetic uses. The work begins with a historical overview of the use of phosphines in metal-free organic reactions, followed by details of their physical properties and the source and preparation methods for representative phosphines and chiral variants. The applications of phosphines as reagents and catalysts in organic synthesis are discussed, along with case studies organized according to reaction type. Researchers, graduate students and undergraduates working in organic synthesis will find this work an invaluable resource. These reactions include halogenation under Appel conditions, Wittig reaction, Staudinger reaction, Mitsunobu reaction, alcohol acylation and kinetic resolution, Rauhut-Currier reaction, Morita-Baylis-Hillman reaction, conjugate addition, umpolung additions, annulation reactions, allylic substitution, allylic amination, and isomerization reactions. For each reaction an overview of the state-of-the-art is presented along with the reaction data, enantioselective version using chiral phosphine, and its application in the synthesis of biologically active compounds and total synthesis of natural products. The work concludes with a summary that highlights the most promising reactions for future development in this field of research.
Sprache
Verlagsort
Zielgruppe
Für höhere Schule und Studium
Graduate students, researchers in academia and industry, undergraduate students
Maße
Höhe: 229 mm
Breite: 152 mm
ISBN-13
978-0-12-814786-3 (9780128147863)
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Schweitzer Klassifikation
Hongchao Guo received his PhD from China Agricultural University in 2002, followed by several years of research at Shanghai Institute of Organic Chemistry, Max-Planck-Institut fuer Kohlenforschung (Muelheim), University of California at Los Angeles and University of Illinois at Urbana-Champaign. In 2010, he joined China Agricultural University as an Associate Professor, and was promoted to Professor in 2011. His research focuses on Lewis base and acid-catalyzed cycloaddition and annulation reactions and their application in organic synthesis. He has published two reviews and more than thirty research papers on phosphine-promoted reactions. Ohyun Kwon, Professor of Chemistry and Biochemistry at UCLA, received her B.S. and M.S. degrees in 1991 and 1993, respectively, from Seoul National University. After receiving her Ph.D. degree in 1998 from Columbia University and, following a postdoctoral stint at Harvard University, Kwon started her independent career in 2001 at UCLA. Her research focuses on phosphine catalysis and its application in total synthesis of natural products. She has played key roles in establishing phosphinocatalysis as one of the main areas of organocatalysis research, and is recognized as one of the leaders in the field.
Autor*in
China Agricultural University, Beijing, China
UCLA Department of Chemistry and Biochemistry, Los Angeles, California, USA
1. Introduction 2. Lewis basicity of phosphines 3. Halogenation and related reactions under Appel conditions 4. Wittig reactions 5. Staudinger reactions 6. Mitsunobu reactions 7. Alcohol acylation and kinetic resolution 8. Rauhut-Currier reactions 9. Morita-Baylis-Hillman reactions 10. Conjugate additions 11. Umpolung additions 12. Annulation reactions 13. Allylic substitution and allylic amination 14. Isomerization 15. Aldol and nitroaldol reaction 16. Ring-opening reaction of epoxides and aziridines 17. Diels-Alder Reactions 18. Miscellaneous reactions 19. Concluding remarks 20. Abbreviations 21. Acknowledgments
