Methods and Applications of Cycloaddition Reactions in Organic Syntheses

by Nishiwaki, Nagatoshi

• ISBN13: 9781118299883
• ISBN10: 1118299884
• eBook ISBN(s): 9781118778180
• Edition: 1st
• Format: Hardcover
• Copyright: 2014-02-10
• Publisher: Wiley
• More Book Details

Summary

Advanced tools for developing new functional materials and applications in chemical research, pharmaceuticals, and materials science

Cycloadditions are among the most useful tools for organic chemists, enabling them to build carbocyclic and heterocyclic structures. These structures can then be used to develop a broad range of functional materials, including pharmaceuticals, agrochemicals, dyes, and optics. With contributions from an international team of leading experts and pioneers in cycloaddition chemistry, this book brings together and reviews recent advances, trends, and emerging research in the field.

Methods and Applications of Cycloaddition Reactions in Organic Syntheses focuses on two component cycloadditions, with chapters covering such topics as:

• N₁ unit transfer reaction to C–C double bonds
• [3+2] Cycloaddition of α, β-unsaturated metal-carbene complexes
• Formal [3+3] cycloaddition approach to natural product synthesis
• Development of new methods for the construction of heterocycles based on cycloaddition reaction of 1,3-dipoles
• Cycloreversion approach for preparation of large π-conjugated compounds
• Transition metal-catalyzed or mediated [5+1] cycloadditions

Readers will learn methods for seamlessly executing important reactions such as Diels-Alder and stereoselective dipolar reactions in order to fabricate heterocyclic compounds, natural products, and functional molecules. The book not only features cutting-edge topics, but also important background information, such as the contributors’ process for developing new methodologies, to help novices become fully adept in the field. References at the end of each chapter lead to original research papers and reviews for facilitating further investigation of individual topics.

Covering the state of the science and technology, Methods and Applications of Cycloaddition Reactions in Organic Syntheses enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.

Author Biography

NAGATOSHI NISHIWAKI, PhD, is Professor of Chemistry at Kochi University of Technology, Japan. Dr. Nishiwaki has published over ninety scientific papers, twenty reviews and book chapters, and ten papers in chemical education. In addition, he has presented his research results at many scientific conferences.

Table of Contents

Part 1. [2+1] Cycloaddition

Chapter 1. [2+1]-type cyclopropanation reactions
Akio Kamimura

Chapter 2. N1 Unit Transfer Reaction to C-C Double Bonds
Satoshi Minakata, Youhei Takada, and Kensuke Kiyokawa

Part 2. [2+2] Cycloaddition

Chapter 3. Lewis Base Catalysed Asymmetric Formal [2+2] Cycloadditions
Andrew Smith, James Douglas, Louis Morrill, and Edward Richmond

Part 3. [2+2] and [4+2]/[2+2] Cycloaddition

Chapter 4. Catalytic [2+2] Cycloaddition of Silyl Enol Ethers
Yosuke Yamaoka and Kiyosei Takasu

Part 4. [3+2] Cycloaddition

Chapter 5. [3+2] Cycloaddition of α,β-Unsaturated Metal-Carbene Complexes
Ryukichi Takagi and Manabu Abe

 Chapter 6. Geometry-Controlled Cycloaddition of C-Alkoxycarbonyl Nitrones: Synthetic Studies on Non-Proteinogenic Amino Acids
Osamu Tamura

Chapter 7. Recent Advances in Catalytic Asymmetric 1,3-Dipolar Cycloadditions of Azomethine Imines, Nitrile Oxides, Diazoalkanes, and Carbonyl Ylides
Hiroyuki Suga and Kennosuke Itoh

Chapter 8. Condensation of Primary Nitro Compounds to Isoxazole Derivatives: Stoichiometric to Catalytic
Francesco De Sarlo and Fabrizio Machetti

 Chapter 9. Carbamoylnitrile Oxide and Inverse Electron-Demand 1,3-Dipolar Cycloaddition
Nagatoshi Nishiwaki and Haruyasu Asahara

Part 5. [3+2], [3+3] and [4+2] Cycloaddition

Chapter 10. Cycloaddition Reactions of Small Rings
Steven D. R. Christie and Hayley T. A. Watson

Part 6. [3+2] and [5+1] Cycloaddition

Chapter 11. Development of New Methods for the Construction of Heterocycles Based on Cycloaddition Reaction of 1,3-Dipoles
Yutaka Ukaji and Takahiro Soeda

Part 7. [3+3] Cycloaddition

Chapter 12. A Formal [3+3] Cycloaddition Approach to Natural Product Synthesis
Jun Deng, Xiao-Na Wang, and Richard P. Hsung

Part 8. [4+2] Cycloaddition

Chapter 13. [4+2]-Cycloaddition Chemistry of Substituted Furans
Scott Bur and Albert Padwa

Chapter 14. Synthesis of Substituted Oligoacenes via Diels?Alder Reactions and Substituent Effects on Molecular Structure, Packing Arrangement, and Solid-state Optical Properties
Chitoshi Kitamura

Chapter 15. Cycloreversion Approach for Preparation of Large π-Conjugated Compounds
Hidemitsu Uno

Part 9. [4+2]/[3+2] Cycloaddition

Chapter 16. Tandem [4+2]/[3+2] cycloadditions
Ramil Y. Baiazitov and Scott E. Denmark

Part 10. [5+1] Cycloaddition

Chapter 17. Transition Metal-Catalyzed or Mediated [5+1] Cycloadditions
Xu-Fei Fu and Zhi-Xiang Yu

Part 11. [4+3] Cycloaddition

Chapter 18. [4+3] Cycloadditions of Enolsilane Derivatives
Sarah Y. Y. Lam and Pauline Chiu

Chapter 19. Application of the [4+3]-Cycloaddition Reaction to the Synthesis of Natural Products
Darin E. Jones and Michael Harmata

Part 12. [5+2] Cycloaddition

Chapter 20. Recent Developments in the [5+2] Cycloaddition
Hervé Clavier and Hélène Pellissier