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

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.

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 Edward
Richmond

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

4 CATALYTIC [2d2] CYCLOADDITION OF SILYL ENOL ETHERS
115

Yosuke Yamaoka and Kiyosei Takasu

PART IV [3+2] CYCLOADDITION

5 [3d2] 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 [3d3] CYCLOADDITION APPROACH TO NATURAL PRODUCT
SYNTHESIS 283

Jun Deng, Xiao-Na Wang, and Richard P. Hsung

PART VIII [4+2] CYCLOADDITION

13 [4d2] 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 [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 THE
SYNTHESIS 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