Domino reactions in organic synthesis 2006 – Tietze

559 Pages·2006·8.23 MB·English

I
Lutz F. Tietze, Gordon Brasche, and
Kersten M. Gericke
Domino Reactions
in Organic Synthesis
DominoReactionsinOrganicSynthesis.LutzF.Tietze,GordonBrasche,andKerstenM.Gericke
Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:3-527-29060-5
II
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III
Lutz F. Tietze, Gordon Brasche,
and Kersten M. Gericke
Domino Reactions
in Organic Synthesis
IV
TheAuthors AllbookspublishedbyWiley-VCHarecarefully
produced.Nevertheless,authors,editors,and
Prof.Dr.Dr.h.c.LutzTietze publisherdonotwarranttheinformationcontained
Inst.f.OrganischeChemie inthesebooks,includingthisbook,tobefreeof
Georg-August-Universität errors.Readersareadvisedtokeepinmindthat
Tammannstr.2 statements,data,illustrations,proceduraldetailsor
37077Göttingen otheritemsmayinadvertentlybeinaccurate.
Dr.GordonBrasche LibraryofCongressCardNo.:
Inst.f.OrganischeChemie appliedfor
Georg-August-Universität
Tammannstr.2 BritishLibraryCataloguing-in-PublicationData
37077Göttingen Acataloguerecordforthisbookisavailablefrom
theBritishLibrary.
Dr.KerstenMatthiasGericke
Inst.f.OrganischeChemie Bibliographicinformationpublishedby
Georg-August-Universität DieDeutscheBibliothek
Tammannstr.2 DieDeutscheBibliothekliststhispublicationinthe
37077Göttingen DeutscheNationalbibliografie;detailedbibliographic
dataisavailableintheInternetat
<http://dnb.ddb.de>.
©2006WILEY-VCHVerlagGmbH&Co.KGaA,
Weinheim
Allrightsreserved(includingthoseoftranslation
intootherlanguages).Nopartofthisbookmaybe
reproducedinanyform−byphotoprinting,
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ISBN-13: 978-3-527-29060-4
ISBN-10: 3-527-29060-5
V
Table of Contents
Introduction 1
Classification 7
1 CationicDominoReactions 11
1.1 Cationic/CationicProcesses 12
1.1.1 Cationic/Cationic/CationicProcesses 33
1.2 Cationic/PericyclicProcesses 39
1.3 Cationic/ReductiveProcesses 42
2 AnionicDominoReactions 48
2.1 Anionic/AnionicProcesses 48
2.1.1 Anionic/Anionic/AnionicProcesses 104
2.1.2 FourfoldandHigherAnionicProcesses 135
2.1.3 Two-andThreefoldAnionicProcessesFollowedbyaNonanionic
Process 142
2.2 Anionic/RadicalProcesses 156
2.3 Anionic/PericyclicProcesses 160
2.3.1 Anionic/PericyclicProcessesFollowedbyFurtherTransformations 185
2.4 Anionic/TransitionMetal-CatalyzedProcesses 191
2.5 Anionic/OxidativeorReductiveProcesses 194
3 RadicalDominoReactions 219
3.1 Radical/CationicDominoProcesses 223
3.2 Radical/AnionicDominoProcesses 224
3.3 Radical/RadicalDominoProcesses 225
3.3.1 Radical/Radical/AnionicDominoProcesses 252
3.3.2 Radical/Radical/RadicalDominoProcesses 253
3.3.3 Radical/Radical/PericyclicDominoProcesses 272
3.3.4 Radical/Radical/OxidationDominoProcesses 273
3.4 Radical/PericyclicDominoProcesses 275
4 PericyclicDominoReactions 280
4.1 Diels−AlderReactions 282
DominoReactionsinOrganicSynthesis.LutzF.Tietze,GordonBrasche,andKerstenM.Gericke
Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:3-527-29060-5
VI TableofContents
4.1.1 Diels−Alder/Diels−AlderReactions 282
4.1.2 Diels−AlderReactions/SigmatropicRearrangements 285
4.1.3 Diels−Alder/Retro-Diels−AlderReactions 289
4.1.4 Diels−AlderReactions/MixedTransformations 290
4.1.5 Hetero-Diels−AlderReactions 297
4.2 1,3-DipolarCycloadditions 303
4.3 [2+2]andHigherCycloadditions 307
4.4 SigmatropicRearrangements 313
4.5 ElectrocyclicReactions 326
4.6 EneReactions 329
4.7 Retro-PericyclicReactions 330
5 PhotochemicallyInducedDominoProcesses 337
5.1 Photochemical/CationicDominoProcesses 337
5.2 Photochemical/AnionicDominoProcesses 339
5.3 Photochemical/RadicalDominoProcesses 344
5.4 Photochemical/PericyclicDominoProcesses 350
5.5 Photochemical/PhotochemicalDominoProcesses 354
5.6 Photochemical/TransitionMetal-CatalyzedDominoProcesses 355
6 TransitionMetal-CatalyzedDominoReactions 359
6.1 Palladium-CatalyzedTransformations 360
6.1.1 TheHeckReaction 362
6.1.1.1 DominoHeckReactions 362
6.1.1.2 Heck/Cross-CouplingReactions 370
6.1.1.3 Heck/Tsuji−TrostReactions 374
6.1.1.4 HeckReactions/CO-Insertions 375
6.1.1.5 HeckReactions/C−H-Activations 376
6.1.1.6 HeckReactions:PericyclicTransformations 379
6.1.1.7 HeckReactions/MixedTransformations 382
6.1.2 Cross-CouplingReactions 386
6.1.2.1 SuzukiReactions 386
6.1.2.2 StilleReactions 388
6.1.2.3 SonogashiraReactions 393
6.1.2.4 OtherCross-CouplingReactions 397
6.1.3 NucleophilicSubstitution(Tsuji−TrostReaction) 398
6.1.4 ReactionsofAlkynesandAllenes 404
6.1.5 OtherPd0-CatalyzedTransformations 411
6.1.6 PdII-CatalyzedTransformations 417
6.2 Rhodium-CatalyzedTransformations 422
6.2.1 FormationofCarbenes 423
6.2.2 Hydroformylations 431
6.2.3 OtherRhodium-CatalyzedTransformations 437
6.3 Ruthenium-CatalyzedTransformations 439
6.3.1 MetathesisReactions 439
6.3.1.1 Metathesis-MetathesisProcesses 441
TableofContents VII
6.3.1.2 Metathesis/HeckReaction/PericyclicReaction/Hydrogenation 451
6.3.2 OtherRuthenium-CatalyzedTransformations 455
6.4 TransitionMetal-CatalyzedTransformationsotherthanPd,Rh,and
Ru 458
6.4.1 Cobalt-InducedTransformations 458
6.4.2 Nickel-InducedTransformations 465
6.4.3 Copper-InducedReactions 470
6.4.4 Tungsten-InducedReactions 475
6.4.5 Molybdenum-InducedReactions 476
6.4.6 Titanium-InducedReactions 477
6.4.7 Chromium-InducedTransformations 479
6.4.8 Platinum-andGold-InducedReactions 480
6.4.9 Iron-andZirconium-InducedReactions 482
6.4.10 Lanthanide-InducedReactions 483
7 DominoReactionsInitiatedbyOxidationorReduction 494
7.1 OxidativeorReductive/CationicDominoProcesses 494
7.2 OxidativeorReductive/AnionicDominoProcesses 496
7.2.1 OxidativeorReductive/Anionic/AnionicDominoProcesses 503
7.2.2 Oxidative/Anionic/PericyclicDominoProcesses 510
7.2.3 OxidativeorReductive/Anionic/OxidativeorReductiveDominoProces-
ses 512
7.3 OxidativeorReductive/PericyclicProcesses 513
7.3.1 Oxidative/Pericyclic/AnionicDominoProcesses 515
7.3.2 OxidativeorReductive/Pericyclic/PericyclicDominoProcesses 518
7.4 OxidativeorReductive/OxidativeorReductiveProcesses 522
8 EnzymesinDominoReactions 529
9 MulticomponentReactions 542
10 SpecialTechniquesinDominoReactions 566
10.1 DominoReactionsunderHighPressure 566
10.2 Solid-Phase-SupportedDominoReactions 569
10.3 Solvent-FreeDominoReactions 574
10.4 Microwave-AssistedDominoReactions 578
10.5 RareMethodsinDominoSynthesis 584
IX
Preface
Theabilitytocreatecomplexmoleculesinonlyafewstepshaslongbeenthedream
ofchemists.ThatsuchthinkingisnotunrealisticcouldbeseenfromNature,where
complicated molecules such as palytoxin, maitotoxin and others are synthesized
withapparenteaseandinahighlyefficientmanner.Now,withthedevelopmentof
dominoreactions,thedreamhasbecomealmosttrueforthelaboratorychemist−
at least partly. Today, this new way of thinking represents a clear change of para-
digminorganicsynthesis,withdominoreactionsbeingfrequentlyusednotonlyin
basicresearchbutalsoinappliedchemistry.
Theuseofdominoreactionshastwomainadvantages.Thefirstadvantageap-
pliestothechemicalindustry,asthecostsnotonlyforwastemanagementbutalso
forenergysuppliesandmaterialsarereduced.Thesecondadvantageisthebenefi-
cialeffectontheenvironment,asdominoreactionshelptosavenaturalresources.
Itis,therefore,notsurprisingthatthisnewconcepthasbeenadoptedveryrapidly
by the scientific community.
Following our first comprehensive review on domino reactions in 1993, which
waspublishedinAngewandteChemie,andasecondreviewin1996inChemicalRe-
views, there has been an “explosion” of publications in this field. In this book we
haveincludedcarefullyidentifiedreactionsequencesandselectedpublicationsup
tothesummerof2005,aswellasdetailsofsomeimportantolderstudiesandvery
recentinvestigationsconductedin2006.Thus,intotal,thebookcontainsover1000
citations!
Atthisstagewewouldliketoapologizefornotincludingallstudiesondomino
reactions,butthiswasduesimplytoalackofspace.Inthisbook,theterm“dom-
ino”isusedthroughouttodescribethereactionsequencesused,andweseekthe
understandingofauthorsoftheincludedpublicationsifwedidnotusetheirter-
minology. Rather, we thought that for a better understanding a unified concept
basedonourdefinitionandclassificationofdominoreactionswouldbemostap-
propriate.Consequently,wewouldverymuchappreciateifeverybodyworkingin
thisfieldwouldinfutureusetheterm“domino”iftheirreactionfulfillsthecondi-
tions of such a transformation.
We would like to thank Jessica Frömmel, Martina Pretor, Sabine Schacht and
especially Katja Schäfer for their continuous help in writing the manuscript and
preparing the schemes. We would also like to thank Dr. Hubertus P. Bell for
manifoldideasandtheselectionofarticles,Dr.SaschaHellkampforcarefulover-
DominoReactionsinOrganicSynthesis.LutzF.Tietze,GordonBrasche,andKerstenM.Gericke
Copyright©2006WILEY-VCHVerlagGmbH&Co.KGaA,Weinheim
ISBN:3-527-29060-5
X Preface
seeingofthemanuscriptandhelpfuladvice,andXiongChenforcontrollingthelit-
erature.WealsoliketothankthepublisherWiley-VCH,andespeciallyWilliamH.
Down,Dr.RomyKirstenandDr.GudrunWalter,fortheirunderstandingandhelp
in preparing the book.
Göttingen, summer 2006 LutzF.Tietze
GordonBrasche
KerstenM.Gericke
XI
Abbreviations
))) Sonification
18-C-6 18-Crown-6 ether
A-3CR (A-4CR)Asingerthree(four)-componentreaction
Ac acetyl
acac acetylacetonato
ACCN 1,1’-azobis(cyclohexanecarbonitrile)
AcOH acetic acid
Ac O acetic anhydride
2
AIBN 2,2’-azobisisobutyronitrile
ALA δ-aminolevulinicacid
ALB AlLibis[(S)-binaphthoxide]complex
All allyl
Ar aryl
BB-4CR Bucherer−Bergsfour-componentreaction
BEH bacterialepoxidehydrolase
BF ·OEt borontrifluoride−diethylethercomplex
3 2
BINAP 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl
BINOL 2,2’-dihydroxy-1,1’-binaphthyl
[bmim]BF 1-butyl-3-methylimidazoliumtetrafluoroborate
4
[bmim]PF 1-butyl-3-methylimidazoliumhexafluorophosphate
6
BMDMS bromomethyldimethylsilyl
Bn benzyl
Boc tert-butoxycarbonyl
BOM benzyloxymethyl
BOXAX 2,2’-bis(oxazolin-2-yl)-1,1’-binaphthyl
BP 1,1’-biphenyl
BS pbromophenylsulphonyloxy
BTIB bis(trifluoroacetoxy)-iodobenzene
Bu n-butyl
Bz benzoyl
CALB Candidaantarcticalipase
CAN cericammoniumnitrate
cat. catalytic; catalyst
Cbz benzyloxycarbonyl