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Methods and Applications of Cycloaddition Reactions in Organic Syntheses


Methods and Applications of Cycloaddition Reactions in Organic Syntheses


1. Aufl.

von: Nagatoshi Nishiwaki

181,99 €

Verlag: Wiley
Format: EPUB
Veröffentl.: 17.12.2013
ISBN/EAN: 9781118778203
Sprache: englisch
Anzahl Seiten: 672

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Beschreibungen

<p><b>Advanced tools for developing new functional materials and applications in chemical research, pharmaceuticals, and materials science</b></p> <p>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.</p> <p><i>Methods and Applications of Cycloaddition Reactions in Organic Syntheses</i> focuses on two component cycloadditions, with chapters covering such topics as:</p> <ul> <li>N<sub>1</sub> unit transfer reaction to C–C double bonds</li> <li>[3+2] Cycloaddition of <i>α, β</i>-unsaturated metal-carbene complexes</li> <li>Formal [3+3] cycloaddition approach to natural product synthesis</li> <li>Development of new methods for the construction of heterocycles based on cycloaddition reaction of 1,3-dipoles</li> <li>Cycloreversion approach for preparation of large <i>π</i>-conjugated compounds</li> <li>Transition metal-catalyzed or mediated [5+1] cycloadditions</li> </ul> <p>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.</p> <p>Covering the state of the science and technology, <i>Methods and Applications of Cycloaddition Reactions in Organic Syntheses</i> enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.</p>
<p><i>PREFACE ix</i></p> <p><i>CONTRIBUTORS xi</i></p> <p><b>PART I [2+1] CYCLOADDITION</b></p> <p>1 [2+1]-TYPE CYCLOPROPANATION REACTIONS 1<br /> <i>Akio Kamimura</i></p> <p>2 N1 UNIT TRANSFER REACTION TO C__C DOUBLE BONDS 67<br /> <i>Satoshi Minakata, Youhei Takeda, and Kensuke Kiyokawa</i></p> <p><b>PART II [2+2] CYCLOADDITION</b></p> <p>3 LEWIS BASE CATALYZED ASYMMETRIC FORMAL [2þ2] CYCLOADDITIONS 89<br /> <i>Andrew D. Smith, James Douglas, Louis C. Morrill, and Edward Richmond</i></p> <p><b>PART III [2+2] AND [4+2]/[2+2] CYCLOADDITION</b></p> <p>4 CATALYTIC [2þ2] CYCLOADDITION OF SILYL ENOL ETHERS 115<br /> <i>Yosuke Yamaoka and Kiyosei Takasu</i></p> <p><b>PART IV [3+2] CYCLOADDITION</b></p> <p>5 [3þ2] CYCLOADDITION OF a,b-UNSATURATED METAL–CARBENE COMPLEXES 135<br /> <i>Ryukichi Takagi and Manabu Abe</i></p> <p>6 GEOMETRY-CONTROLLED CYCLOADDITION OF C-ALKOXYCARBONYL NITRONES: SYNTHETIC STUDIES ON NONPROTEINOGENIC AMINO ACIDS 151<br /> <i>Osamu Tamura</i></p> <p>7 RECENT ADVANCES IN CATALYTIC ASYMMETRIC 1,3-DIPOLAR CYCLOADDITIONS OF AZOMETHINE IMINES, NITRILE OXIDES, DIAZOALKANES, AND CARBONYL YLIDES 175<br /> <i>Hiroyuki Suga and Kennosuke Itoh</i></p> <p>8 CONDENSATION OF PRIMARY NITRO COMPOUNDS TO ISOXAZOLE DERIVATIVES: STOICHIOMETRIC TO CATALYTIC 205<br /> <i>Francesco De Sarlo and Fabrizio Machetti</i></p> <p>9 CARBAMOYLNITRILE OXIDE AND INVERSE ELECTRON-DEMAND 1,3-DIPOLAR CYCLOADDITION 223<br /> <i>Nagatoshi Nishiwaki and Haruyasu Asahara</i></p> <p><b>PART V [3+2], [3+3], AND [4+2] CYCLOADDITION</b></p> <p>10 CYCLOADDITION REACTIONS OF SMALL RINGS 241<br /> <i>Steven D. R. Christie and Hayley T. A. Watson</i></p> <p><b>PART VI [3+2] AND [5+1] CYCLOADDITION</b></p> <p>11 DEVELOPMENT OF NEW METHODS FOR THE CONSTRUCTION OF HETEROCYCLES BASED ON CYCLOADDITION REACTION OF 1,3-DIPOLES 263<br /> <i>Yutaka Ukaji and Takahiro Soeta</i></p> <p><b>PART VII [3+3] CYCLOADDITION</b></p> <p>12 A FORMAL [3þ3] CYCLOADDITION APPROACH TO NATURAL PRODUCT SYNTHESIS 283<br /> <i>Jun Deng, Xiao-Na Wang, and Richard P. Hsung</i></p> <p><b>PART VIII [4+2] CYCLOADDITION</b></p> <p>13 [4þ2] CYCLOADDITION CHEMISTRY OF SUBSTITUTED FURANS 355<br /> <i>Scott Bur and Albert Padwa</i></p> <p>14 SYNTHESIS OF SUBSTITUTED OLIGOACENES VIA DIELS–ALDER REACTIONS AND SUBSTITUENT EFFECTS ON MOLECULAR STRUCTURE, PACKING ARRANGEMENT, AND SOLID-STATE OPTICAL PROPERTIES 407<br /> <i>Chitoshi Kitamura</i></p> <p>15 CYCLOREVERSION APPROACH FOR PREPARATION OF LARGE p-CONJUGATED COMPOUNDS 429<br /> <i>Hidemitsu Uno</i></p> <p><b>PART IX [4+2]/[3+2] CYCLOADDITION</b></p> <p>16 TANDEM [4þ2]/[3þ2] CYCLOADDITIONS 471<br /> <i>Ramil Y. Baiazitov and Scott E. Denmark</i></p> <p><b>PART X [5+1] CYCLOADDITION</b></p> <p>17 TRANSITION METAL-CATALYZED OR -MEDIATED [5þ1] CYCLOADDITIONS 551<br /> <i>Xu-Fei Fu and Zhi-Xiang Yu</i></p> <p><b>PART XI [4+3] CYCLOADDITION</b></p> <p>18 [4þ3] CYCLOADDITIONS OF ENOLSILANE DERIVATIVES 565<br /> <i>Sarah Y. Y. Lam and Pauline Chiu</i></p> <p>19 APPLICATION OF THE [4þ3] CYCLOADDITION REACTION TO THE SYNTHESIS OF NATURAL PRODUCTS 599<br /> <i>Darin E. Jones and Michael Harmata</i></p> <p><b>PART XII [5+2] CYCLOADDITION</b></p> <p>20 RECENT DEVELOPMENTS IN THE [5þ2] CYCLOADDITION 631<br /> <i>Hervé Clavier and Hélène Pellissier</i></p> <p><i>INDEX 655</i></p>
<p><b>NAGATOSHI NISHIWAKI, PhD,</b> 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.</p>
<p><b>Advanced tools for developing new functional materials and applications in chemical research, pharmaceuticals, and materials science</b></p> <p>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.</p> <p><i>Methods and Applications of Cycloaddition Reactions in Organic Syntheses</i> focuses on two component cycloadditions, with chapters covering such topics as:</p> <ul> <li>N<sub>1</sub> unit transfer reaction to C–C double bonds</li> <li>[3+2] Cycloaddition of <i>α, β</i>-unsaturated metal-carbene complexes</li> <li>Formal [3+3] cycloaddition approach to natural product synthesis</li> <li>Development of new methods for the construction of heterocycles based on cycloaddition reaction of 1,3-dipoles</li> <li>Cycloreversion approach for preparation of large <i>π</i>-conjugated compounds</li> <li>Transition metal-catalyzed or mediated [5+1] cycloadditions</li> </ul> <p>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.</p> <p>Covering the state of the science and technology, <i>Methods and Applications of Cycloaddition Reactions in Organic Syntheses</i> enables synthetic organic chemists to advance their research and develop new functional materials and applications in chemical research, pharmaceuticals, and materials science.</p>

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