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Methods and Applications of Cycloaddition Reactions in Organic Syntheses

ISBN: 978-1-118-29988-3
672 pages
February 2014
Methods and Applications of Cycloaddition Reactions in Organic Syntheses (1118299884) cover image

Description

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.

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Table of Contents

PREFACE ix

CONTRIBUTORS xi

PART I [2+1] CYCLOADDITION

1 [2+1]-TYPE CYCLOPROPANATION REACTIONS 1
Akio Kamimura

2 N1 UNIT TRANSFER REACTION TO C__C DOUBLE BONDS 67
Satoshi Minakata, Youhei Takeda, and Kensuke Kiyokawa

PART II [2+2] CYCLOADDITION

3 LEWIS BASE CATALYZED ASYMMETRIC FORMAL [2þ2] CYCLOADDITIONS 89
Andrew D. Smith, James Douglas, Louis C. Morrill, and Edward Richmond

PART III [2+2] AND [4+2]/[2+2] CYCLOADDITION

4 CATALYTIC [2þ2] CYCLOADDITION OF SILYL ENOL ETHERS 115
Yosuke Yamaoka and Kiyosei Takasu

PART IV [3+2] CYCLOADDITION

5 [3þ2] CYCLOADDITION OF a,b-UNSATURATED METAL–CARBENE COMPLEXES 135
Ryukichi Takagi and Manabu Abe

6 GEOMETRY-CONTROLLED CYCLOADDITION OF C-ALKOXYCARBONYL NITRONES: SYNTHETIC STUDIES ON NONPROTEINOGENIC AMINO ACIDS 151
Osamu Tamura

7 RECENT ADVANCES IN CATALYTIC ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS OF AZOMETHINE IMINES, NITRILE OXIDES, DIAZOALKANES, AND CARBONYL YLIDES 175
Hiroyuki Suga and Kennosuke Itoh

8 CONDENSATION OF PRIMARY NITRO COMPOUNDS TO ISOXAZOLE DERIVATIVES: STOICHIOMETRIC TO CATALYTIC 205
Francesco De Sarlo and Fabrizio Machetti

9 CARBAMOYLNITRILE OXIDE AND INVERSE ELECTRON-DEMAND 1,3-DIPOLAR CYCLOADDITION 223
Nagatoshi Nishiwaki and Haruyasu Asahara

PART V [3+2], [3+3], AND [4+2] CYCLOADDITION

10 CYCLOADDITION REACTIONS OF SMALL RINGS 241
Steven D. R. Christie and Hayley T. A. Watson

PART VI [3+2] AND [5+1] CYCLOADDITION

11 DEVELOPMENT OF NEW METHODS FOR THE CONSTRUCTION OF HETEROCYCLES BASED ON CYCLOADDITION REACTION OF 1,3-DIPOLES 263
Yutaka Ukaji and Takahiro Soeta

PART VII [3+3] CYCLOADDITION

12 A FORMAL [3þ3] CYCLOADDITION APPROACH TO NATURAL PRODUCT SYNTHESIS 283
Jun Deng, Xiao-Na Wang, and Richard P. Hsung

PART VIII [4+2] CYCLOADDITION

13 [4þ2] CYCLOADDITION CHEMISTRY OF SUBSTITUTED FURANS 355
Scott Bur and Albert Padwa

14 SYNTHESIS OF SUBSTITUTED OLIGOACENES VIA DIELS–ALDER REACTIONS AND SUBSTITUENT EFFECTS ON MOLECULAR STRUCTURE, PACKING ARRANGEMENT, AND SOLID-STATE OPTICAL PROPERTIES 407
Chitoshi Kitamura

15 CYCLOREVERSION APPROACH FOR PREPARATION OF LARGE p-CONJUGATED COMPOUNDS 429
Hidemitsu Uno

PART IX [4+2]/[3+2] CYCLOADDITION

16 TANDEM [4þ2]/[3þ2] CYCLOADDITIONS 471
Ramil Y. Baiazitov and Scott E. Denmark

PART X [5+1] CYCLOADDITION

17 TRANSITION METAL-CATALYZED OR -MEDIATED [5þ1] CYCLOADDITIONS 551
Xu-Fei Fu and Zhi-Xiang Yu

PART XI [4+3] CYCLOADDITION

18 [4þ3] CYCLOADDITIONS OF ENOLSILANE DERIVATIVES 565
Sarah Y. Y. Lam and Pauline Chiu

19 APPLICATION OF THE [4þ3] CYCLOADDITION REACTION TO THE SYNTHESIS OF NATURAL PRODUCTS 599
Darin E. Jones and Michael Harmata

PART XII [5+2] CYCLOADDITION

20 RECENT DEVELOPMENTS IN THE [5þ2] CYCLOADDITION 631
Hervé Clavier and Hélène Pellissier

INDEX 655

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Author Information

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.

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