Methods and Applications of Cycloaddition Reactions in Organic Syntheses

673 Pages·2014·10.539 MB·English

by  Nishiwaki, Nagatoshi

METHODS AND APPLICATIONS
OF CYCLOADDITION REACTIONS
IN ORGANIC SYNTHESES

METHODS AND APPLICATIONS
OF CYCLOADDITION REACTIONS
IN ORGANIC SYNTHESES
Edited by
NAGATOSHI NISHIWAKI
Kochi University of Technology
Kami, Kochi, Japan
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LibraryofCongressCataloging-in-PublicationData:
Methodsandapplicationsofcycloadditionreactionsinorganicsyntheses/
[editedby]NagatoshiNishiwaki,KochiUniversityofTechnology,Kami,Kochi,Japan.
pagescm
Includesbibliographicalreferencesandindex.
ISBN978-1-118-29988-3(cloth)
1. Organiccompounds–Synthesis. 2. Ringformation(Chemistry) I. Nishiwaki,Nagatoshi,1963-editor
ofcompilation.
QD262.M542014
5470.27–dc23
2013023528
PrintedintheUnitedStatesofAmerica
10 9 8 7 6 5 4 3 2 1
CONTENTS
PREFACE ix
CONTRIBUTORS xi
PARTI [2+1]CYCLOADDITION
1 [2+1]-TYPECYCLOPROPANATIONREACTIONS 1
AkioKamimura
2 N UNITTRANSFERREACTIONTOC(cid:1)(cid:1)CDOUBLEBONDS 67
1
SatoshiMinakata,YouheiTakeda,andKensukeKiyokawa
PARTII [2+2]CYCLOADDITION
3 LEWISBASECATALYZEDASYMMETRICFORMAL[2þ2]
CYCLOADDITIONS 89
AndrewD.Smith,JamesDouglas,LouisC.Morrill,andEdwardRichmond
PARTIII [2+2]AND[4+2]/[2+2]CYCLOADDITION
4 CATALYTIC[2þ2]CYCLOADDITIONOFSILYLENOLETHERS 115
YosukeYamaokaandKiyoseiTakasu
PARTIV [3+2]CYCLOADDITION
5 [3þ2]CYCLOADDITIONOFa,b-UNSATURATEDMETAL–CARBENE
COMPLEXES 135
RyukichiTakagiandManabuAbe
v
vi CONTENTS
6 GEOMETRY-CONTROLLEDCYCLOADDITIONOF
C-ALKOXYCARBONYLNITRONES:SYNTHETICSTUDIES
ONNONPROTEINOGENICAMINOACIDS 151
OsamuTamura
7 RECENTADVANCESINCATALYTICASYMMETRIC1,3-DIPOLAR
CYCLOADDITIONSOFAZOMETHINEIMINES,NITRILEOXIDES,
DIAZOALKANES,ANDCARBONYLYLIDES 175
HiroyukiSugaandKennosukeItoh
8 CONDENSATIONOFPRIMARYNITROCOMPOUNDSTO
ISOXAZOLEDERIVATIVES:STOICHIOMETRICTOCATALYTIC 205
FrancescoDeSarloandFabrizioMachetti
9 CARBAMOYLNITRILEOXIDEANDINVERSEELECTRON-DEMAND
1,3-DIPOLARCYCLOADDITION 223
NagatoshiNishiwakiandHaruyasuAsahara
PARTV [3+2],[3+3],AND[4+2]CYCLOADDITION
10 CYCLOADDITIONREACTIONSOFSMALLRINGS 241
StevenD.R.ChristieandHayleyT.A.Watson
PARTVI [3+2]AND[5+1]CYCLOADDITION
11 DEVELOPMENTOFNEWMETHODSFORTHECONSTRUCTION
OFHETEROCYCLESBASEDONCYCLOADDITIONREACTION
OF1,3-DIPOLES 263
YutakaUkajiandTakahiroSoeta
PARTVII [3+3]CYCLOADDITION
12 AFORMAL[3þ3]CYCLOADDITIONAPPROACHTONATURAL
PRODUCTSYNTHESIS 283
JunDeng,Xiao-NaWang,andRichardP.Hsung
PARTVIII [4+2]CYCLOADDITION
13 [4þ2]CYCLOADDITIONCHEMISTRYOFSUBSTITUTEDFURANS 355
ScottBurandAlbertPadwa
14 SYNTHESISOFSUBSTITUTEDOLIGOACENESVIADIELS–ALDER
REACTIONSANDSUBSTITUENTEFFECTSONMOLECULAR
STRUCTURE,PACKINGARRANGEMENT,ANDSOLID-STATE
OPTICALPROPERTIES 407
ChitoshiKitamura
15 CYCLOREVERSIONAPPROACHFORPREPARATIONOFLARGE
p-CONJUGATEDCOMPOUNDS 429
HidemitsuUno
CONTENTS vii
PARTIX [4+2]/[3+2]CYCLOADDITION
16 TANDEM[4þ2]/[3þ2]CYCLOADDITIONS 471
RamilY.BaiazitovandScottE.Denmark
PARTX [5+1]CYCLOADDITION
17 TRANSITIONMETAL-CATALYZEDOR-MEDIATED[5þ1]
CYCLOADDITIONS 551
Xu-FeiFuandZhi-XiangYu
PARTXI [4+3]CYCLOADDITION
18 [4þ3]CYCLOADDITIONSOFENOLSILANEDERIVATIVES 565
SarahY.Y.LamandPaulineChiu
19 APPLICATIONOFTHE[4þ3]CYCLOADDITIONREACTION
TOTHESYNTHESISOFNATURALPRODUCTS 599
DarinE.JonesandMichaelHarmata
PARTXII [5+2]CYCLOADDITION
20 RECENTDEVELOPMENTSINTHE[5þ2]CYCLOADDITION 631
Herv(cid:1)eClavierandH(cid:1)el(cid:3)enePellissier
INDEX 655