Methods and Applications of Cycloaddition Reactions in Organic Syntheses (Hardcover)

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