Methods and Applications of Cycloaddition Reactions in Organic Syntheses

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 [2?2] 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 [2?2] CYCLOADDITION OF SILYL ENOL ETHERS 115 Yosuke Yamaoka and Kiyosei Takasu PART IV [3+2] CYCLOADDITION 5 [3?2] 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 [3?3] CYCLOADDITION APPROACH TO NATURAL PRODUCT SYNTHESIS 283 Jun Deng, Xiao-Na Wang, and Richard P. Hsung PART VIII [4+2] CYCLOADDITION 13 [4?2] 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 [4?2]/[3?2] CYCLOADDITIONS 471 Ramil Y. Baiazitov and Scott E. Denmark PART X [5+1] CYCLOADDITION 17 TRANSITION METAL-CATALYZED OR -MEDIATED [5?1] CYCLOADDITIONS 551 Xu-Fei Fu and Zhi-Xiang Yu PART XI [4+3] CYCLOADDITION 18 [4?3] CYCLOADDITIONS OF ENOLSILANE DERIVATIVES 565 Sarah Y. Y. Lam and Pauline Chiu 19 APPLICATION OF THE [4?3] 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 [5?2] CYCLOADDITION 631 Hervé Clavier and Hélène Pellissier INDEX 655