Nishiwaki Methods and Applications of Cycloaddition Reactions in Organic Syntheses

1. Auflage 2013
ISBN: 978-1-118-77820-3
Verlag: John Wiley & Sons
Format: EPUB
Kopierschutz: 0 - No protection

E-Book, Englisch, 512 Seiten, E-Book

Advanced tools for developing new functional materials andapplications in chemical research, pharmaceuticals, and materialsscience
Cycloadditions are among the most useful tools for organicchemists, enabling them to build carbocyclic and heterocyclicstructures. These structures can then be used to develop a broadrange of functional materials, including pharmaceuticals,agrochemicals, dyes, and optics. With contributions from aninternational team of leading experts and pioneers in cycloadditionchemistry, this book brings together and reviews recent advances,trends, and emerging research in the field.
Methods and Applications of Cycloaddition Reactions inOrganic Syntheses focuses on two component cycloadditions, withchapters covering such topics as:
* N1 unit transfer reaction to C-C doublebonds
* [3+2] Cycloaddition of alpha, beta-unsaturatedmetal-carbene complexes
* Formal [3+3] cycloaddition approach to natural productsynthesis
* Development of new methods for the construction of heterocyclesbased on cycloaddition reaction of 1,3-dipoles
* Cycloreversion approach for preparation of largepi-conjugated compounds
* Transition metal-catalyzed or mediated [5+1]cycloadditions
Readers will learn methods for seamlessly executing importantreactions such as Diels-Alder and stereoselective dipolar reactionsin order to fabricate heterocyclic compounds, natural products, andfunctional molecules. The book not only features cutting-edgetopics, but also important background information, such as thecontributors' process for developing new methodologies, tohelp novices become fully adept in the field. References at the endof each chapter lead to original research papers and reviews forfacilitating further investigation of individual topics.
Covering the state of the science and technology, Methods andApplications of Cycloaddition Reactions in Organic Synthesesenables synthetic organic chemists to advance their research anddevelop new functional materials and applications in chemicalresearch, pharmaceuticals, and materials science.

Autoren/Hrsg.

Nishiwaki, Nagatoshi

Inhaltsverzeichnis

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 [2d2]CYCLOADDITIONS 89
Andrew D. Smith, James Douglas, Louis C. Morrill, and EdwardRichmond
PART III [2+2] AND [4+2]/[2+2] CYCLOADDITION
4 CATALYTIC [2d2] CYCLOADDITION OF SILYL ENOL ETHERS115
Yosuke Yamaoka and Kiyosei Takasu
PART IV [3+2] CYCLOADDITION
5 [3d2] CYCLOADDITION OF a,b-UNSATURATEDMETAL-CARBENE COMPLEXES 135
Ryukichi Takagi and Manabu Abe
6 GEOMETRY-CONTROLLED CYCLOADDITION OF C-ALKOXYCARBONYLNITRONES: SYNTHETIC STUDIES ON NONPROTEINOGENIC AMINO ACIDS151
Osamu Tamura
7 RECENT ADVANCES IN CATALYTIC ASYMMETRIC 1,3-DIPOLARCYCLOADDITIONS OF AZOMETHINE IMINES, NITRILE OXIDES, DIAZOALKANES,AND CARBONYL YLIDES 175
Hiroyuki Suga and Kennosuke Itoh
8 CONDENSATION OF PRIMARY NITRO COMPOUNDS TO ISOXAZOLEDERIVATIVES: STOICHIOMETRIC TO CATALYTIC 205
Francesco De Sarlo and Fabrizio Machetti
9 CARBAMOYLNITRILE OXIDE AND INVERSE ELECTRON-DEMAND 1,3-DIPOLARCYCLOADDITION 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 OFHETEROCYCLES BASED ON CYCLOADDITION REACTION OF 1,3-DIPOLES263
Yutaka Ukaji and Takahiro Soeta
PART VII [3+3] CYCLOADDITION
12 A FORMAL [3d3] CYCLOADDITION APPROACH TO NATURAL PRODUCTSYNTHESIS 283
Jun Deng, Xiao-Na Wang, and Richard P. Hsung
PART VIII [4+2] CYCLOADDITION
13 [4d2] CYCLOADDITION CHEMISTRY OF SUBSTITUTED FURANS355
Scott Bur and Albert Padwa
14 SYNTHESIS OF SUBSTITUTED OLIGOACENES VIA DIELS-ALDERREACTIONS AND SUBSTITUENT EFFECTS ON MOLECULAR STRUCTURE, PACKINGARRANGEMENT, AND SOLID-STATE OPTICAL PROPERTIES 407
Chitoshi Kitamura
15 CYCLOREVERSION APPROACH FOR PREPARATION OF LARGE p-CONJUGATEDCOMPOUNDS 429
Hidemitsu Uno
PART IX [4+2]/[3+2] CYCLOADDITION
16 TANDEM [4d2]/[3d2] CYCLOADDITIONS 471
Ramil Y. Baiazitov and Scott E. Denmark
PART X [5+1] CYCLOADDITION
17 TRANSITION METAL-CATALYZED OR -MEDIATED [5d1]CYCLOADDITIONS 551
Xu-Fei Fu and Zhi-Xiang Yu
PART XI [4+3] CYCLOADDITION
18 [4d3] CYCLOADDITIONS OF ENOLSILANE DERIVATIVES 565
Sarah Y. Y. Lam and Pauline Chiu
19 APPLICATION OF THE [4d3] CYCLOADDITION REACTION TO THESYNTHESIS OF NATURAL PRODUCTS 599
Darin E. Jones and Michael Harmata
PART XII [5+2] CYCLOADDITION
20 RECENT DEVELOPMENTS IN THE [5d2] CYCLOADDITION 631
Hervé Clavier and Hélène Pellissier
INDEX 655

Über Autor(innen)

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