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首页 有机合成中命名反应的战略性应用

有机合成中命名反应的战略性应用.pdf

有机合成中命名反应的战略性应用

贺华平
2010-08-14 0人阅读 举报 0 0 暂无简介

简介:本文档为《有机合成中命名反应的战略性应用pdf》,可适用于工程科技领域

TABLEOFCONTENTSSEARCHTEXTStrategicApplicationsofNamedReactionsinOrganicSynthesisMAINMENUprovidedbywjswiftYiLuanTABLEOFCONTENTSSEARCHTEXTiiTABLEOFCONTENTSSEARCHTEXTiiiStrategicApplicationsofNamedReactionsinOrganicSynthesisBackgroundandDetailedMechanismsbyLászlóKürtiandBarbaraCzakóUNIVERSITYOFPENNSYLVANIANamedReactionsAMSTERDAM•BOSTON•HEIDELBERG•LONDON•NEWYORK•OXFORD•PARISSANDIEGO•SANFRANCISCO•SINGAPORE•SYDNEY•TOKYOTABLEOFCONTENTSSEARCHTEXTivSeniorPublishingEditorJeremyHayhurstProjectManagerCarlMSoaresEditorialAssistantDesireeMarrMarketingManagerLindaBeattieCoverPrinterRRDonnelleyInteriorPrinterRRDonnelleyElsevierAcademicPressCorporateDrive,Suite,Burlington,MA,USABStreet,Suite,SanDiego,California,USATheobald'sRoad,LondonWCXRR,UKThisbookisprintedonacidfreepaperCopyright©,ElsevierIncAllrightsreservedNopartofthispublicationmaybereproducedortransmittedinanyformorbyanymeans,electronicormechanical,includingphotocopy,recording,oranyinformationstorageandretrievalsystem,withoutpermissioninwritingfromthepublisherPermissionsmaybesoughtdirectlyfromElsevier’sScienceTechnologyRightsDepartmentinOxford,UK:phone:(),fax:(),email:permissionselseviercomukYoumayalsocompleteyourrequestonlineviatheElsevierhomepage(http:elseviercom),byselecting“CustomerSupport”andthen“ObtainingPermissions”LibraryofCongressCataloginginPublicationDataApplicationSubmittedBritishLibraryCataloguinginPublicationDataAcataloguerecordforthisbookisavailablefromtheBritishLibraryISBN:ForallinformationonallElsevierAcademicPressPublicationsvisitourWebsiteatwwwbookselseviercomPrintedintheUnitedStatesofAmericaTABLEOFCONTENTSSEARCHTEXTvThisbookisdedicatedtoProfessorMadeleineMJoulliéforherlifelongcommitmenttomentoringgraduatestudentsTABLEOFCONTENTSSEARCHTEXTviTABLEOFCONTENTSSEARCHTEXTviiABOUTTHEAUTHORSBarbaraCzakówasbornandraisedinHungaryShereceivedherDiplomafromLajosKossuthUniversityinDebrecen,Hungary(nowUniversityofDebrecen)SheobtainedherMasterofSciencedegreeatUniversityofMissouriColumbiaCurrentlysheispursuingherPhDdegreeinsyntheticorganicchemistryunderthesupervisionofProfessorGaryAMolanderattheUniversityofPennsylvaniaLászlóKürtiwasbornandraisedinHungaryHereceivedhisDiplomafromLajosKossuthUniversityinDebrecen,Hungary(nowUniversityofDebrecen)HeobtainedhisMasterofSciencedegreeatUniversityofMissouriColumbiaCurrentlyheispursuinghisPhDdegreeinsyntheticorganicchemistryunderthesupervisionofProfessorAmosBSmithIIIattheUniversityofPennsylvaniaTABLEOFCONTENTSSEARCHTEXTviiiACKNOWLEDGEMENTSTheroadthatledtothecompletionofthisbookwasdifficult,however,weenjoyedthesupportofmanywonderfulpeoplewhoguidedandhelpedusalongthewayThemostinfluentialpersonwasProfessorMadeleineMJoulliéwhoseinsight,honestcriticismandinvaluablesuggestionshelpedtomoldthemanuscriptintoitscurrentformWhenwecompletedhalfofthemanuscriptinearly,ProfessorAmosBSmithIIIwasteachinghissynthesisclass"StrategiesandTacticsinOrganicSynthesis"andadoptedthemanuscriptWewouldliketothankhimforhissupportandencouragementWealsothankthestudentsinhisclassfortheirusefulobservationsthataidedthedesignofanumberofdifficultschemesOurthanksalsogotoProfessorGaryAMolanderforhisvaluableremarksregardingtheorganometallicreactionsHehadseveralexcellentsuggestionsonwhichnamedreactionstoincludeEarlierthisyearourpublisher,AcademicPressElsevierScience,sentthemanuscripttoanumberofresearchgroupsintheUSaswellasintheUKThethoroughreviewconductedbytheprofessorsandinsomecasesalsobyvolunteergraduatestudentsisgreatlyappreciatedTheyare(inalphabeticalorder):ProfessorDonaldHAue(UniversityofCaliforniaSantaBarbara)ProfessorIanFleming(UniversityofCambridge,UK)ProfessorRainerGlaser(UniversityofMissouriColumbia)ProfessorMichaelHarmata(UniversityofMissouriColumbia)ProfessorRobertAWJohnstone(UniversityofLiverpool,UK)ProfessorErikJSorensen(PrincetonUniversity)ProfessorPAWender(StanfordUniversity)andtwoofhisgraduatestudentsCindyKanandJohnKowalskiProfessorPeterWipf(UniversityofPittsburgh)WewouldliketoexpressourgratitudetothefollowingfriendscolleagueswhohavecarefullyreadmultipleversionsofthemanuscriptandwethankthemfortheexcellentremarksandhelpfuldiscussionsTheywereinstrumentalinmakingthemanuscriptasaccurateanderrorfreeaspossible:JamesPCarey(MerckResearchLaboratories)AkinHDavulcu(BristolMyersSquibbUniversityofPennsylvania)DrMehmetKahraman(Kalypsys,Inc)JustinRagains(UniversityofPennsylvania)ThomasRazler(UniversityofPennsylvania)TherewereseveralotherfriendscolleagueswhoreviewedcertainpartsofthemanuscriptorearlierversionsandgaveusvaluablefeedbackonthecontentaswellasinthedesignoftheschemesClayBennett(UniversityofPennsylvania)ProfCheonGyuCho(HanyangUniversity,KoreaUniversityofPennsylvania)DrShaneFoister(UniversityofPennsylvania)DrEugenMesaros(UniversityofPennsylvania)DrEmmanuelMeyer(UniversityofPennsylvania)DavidJStJean,Jr(UniversityofPennsylvania)DrKirstenZeitler(UniversityofRegensburg,Germany)Finally,wewouldliketothankoureditoratElsevier,JeremyHayhurst,whogaveusthechancetomakeacontributiontotheeducationofgraduatestudentsinthefieldoforganicchemistryHegenerouslyapprovedallofourrequestsfortechnicalsupportthushelpingustremendouslytofinishthewritinginarecordamountoftimeOurspecialthanksareextendedtoeditorialassistantsDesireéMarrandpreviously,NoraDonaghy,whohelpedconductthereviewsandmadesurethatwedidnotgetlostinamazeofdocumentsTABLEOFCONTENTSSEARCHTEXTMAINMENUMAINMENUCONTENTSIForewordbyEJCoreyxIIIntroductionbyKCNicolaouxiIIIPrefacexiiIVExplanationoftheUseofColorsintheSchemesandTextxivVListofAbbreviationsxviiVIListofNamedOrganicReactionsxlvVIINamedOrganicReactionsinAlphabeticalOrderVIIIAppendix:ListingoftheNamedReactionsbySyntheticTypeandbytheirUtilityBriefexplanationoftheorganizationofthissectionListofnamedreactionsinchronologicalorderoftheirdiscoveryReactioncategories–CategorizationofnamedreactionsintabularformatAffectedfunctionalgroups–ListingoftransformationsintabularformatPreparationoffunctionalgroups–ListingoftransformationsintabularformatIXReferencesXIndexTABLEOFCONTENTSSEARCHTEXTxFOREWORDThisbookon"StrategicApplicationsofNamedReactionsinOrganicSynthesis"isdestinedtobecomeunusuallyuseful,valuable,andinfluentialforadvancedstudentsandresearchersinthefieldItbreaksnewgroundinmanywaysandsetsanadmirablestandardforthenextgenerationoftextsandreferenceworksItsvirtuesaresonumerousthereisaproblemindecidingwheretobeginMyfirstimpressionuponopeningthebookwasthattheappearanceofitspagesisuniformlyelegantandpleasing–fromtheformulagraphics,totheprint,tothelayout,andtothelogicalorganizationandformatTheauthorsemployfourcolorgraphicsinathoughtfulandeffectivewayAllthechemicalformulasareexquisitelydrawnThebookcoversmanyvariedandusefulreactionsforthesynthesisofcomplexmolecules,andinaremarkablyclear,authoritativeandbalancedway,consideringthatonlytwopagesareallocatedforeachThisisdonewithunusualrigorandattentiontodetailPackedwithineachtwopagesectionarehistoricalbackground,aconciseexpositionofreactionmechanismandsalientandorrecentapplicationsThecontextofeachexampleismadecrystalclearbytheinclusionofthestructureofthefinalsynthetictargetThereferencingiseclecticbutextensiveanduptodateimportantreviewsareincludedTheamountofinformationthatisimportantforchemistsworkingatthefrontiersofsynthesistoknowistrulyenormous,andalsoconstantlygrowingForayoungchemistinthisfield,thereissomuchtolearnthatthesubjectisattheveryleastdauntingItwouldbewellneighimpossiblewereitnotfortheeffortsofcountlessauthorsoftextbooksandreviewsThisbookrepresentsaveryefficientandattractivewayforwardandamodelforfutureauthorsIfIwereastudentofsyntheticchemistry,IwouldreadthisvolumesectionbysectionandkeepitcloseathandforreferenceandfurtherstudyIextendcongratulationstoLászlóKürtiandBarbaraCzakóforatrulyfineaccomplishmentandamassiveamountofworkthatmadeitpossibleThescholarshipandcarethattheybroughttothistaskwillbewidelyappreciatedbecausetheyleapoutofeachpageIhopethatthiswonderfulteamwillconsiderextendingtheirjointventuretootherregionsofsyntheticchemicalspaceJobwelldone!EJCoreyJanuary,TABLEOFCONTENTSSEARCHTEXTxiINTRODUCTIONThefieldofchemicalsynthesiscontinuestoamazewithitsgrowingandimpressivepowertoconstructincreasinglycomplexanddiversemoleculararchitecturesBeingtheprecisesciencethatitis,thisdisciplineoftenextendsnotonlyintotherealmsoftechnology,butalsointothedomainsofthefinearts,foritengendersunparallelpotentialforcreativityandimaginationinitspracticeEnterprisesinchemicalsynthesisencompassboththediscoveryanddevelopmentofpowerfulreactionsandtheinventionofsyntheticstrategiesfortheconstructionofdefinedtargetmolecules,naturalordesigned,moreorlesscomplexWhilestudiesintheformerarea–syntheticmethodology–fuelandenablestudiesinthelatter–targetsynthesis–thelatterfieldoffersatestinggroundfortheformerBlendingthetwoareasprovidesforanexcitingendeavortocontemplate,experience,andwatchTheenduringartoftotalsynthesis,inparticular,affordsthemoststringenttestofchemicalreactions,oldandnew,namedandunnamed,whileitsoverallreachandefficiencyprovidesameasureofitsconditionatanygiventimeTheinterplayoftotalsynthesisanditstools,thechemicalreactions,isafascinatingsubjectwhetheritiswritten,read,orpracticedThissuperbvolumebyLászlóKürtiandBarbaraCzakódemonstratesclearlythepowerandbeautyofthisblendofscienceandartTheauthorshavedevelopedastandardtwopageformatfordiscussingeachoftheirselectionswherebyeachnamedreactionisconciselyintroduced,mechanisticallyexplained,andappropriatelyexemplifiedwithhighlightsofconstructionsofnaturalproducts,keyintermediatesandotherimportantmoleculesTheseliteraturehighlightsarearealtreasuretroveofinformationandajoytoread,bringingeachnamedreactiontolifeandconveyingastrongsenseofitsutilityanddynamismTheinclusionofanuptodatereferencelistingoffersacompleteoverviewofeachreactionatone’sfingertipsThevastwealthofinformationsoeffectivelycompiledinthiscolorfultextwillnotonlyprovetobeextraordinarilyusefultostudentsandpractitionersoftheartofchemicalsynthesis,butwillalsohelpfacilitatetheshapingofitsfutureasitmovesforwardintoeverhigherlevelsofcomplexity,diversityandefficiencyThevitalityoftheenduringfieldoftotalsynthesisexudesfromthisbook,captivatingtheattentionofthereaderthroughoutTheauthorsaretobecongratulatedfortherichandlivelystyletheydevelopedandwhichtheysoeffectivelyemployedintheirdidacticandaestheticallypleasingpresentationsTheessenceoftheartandscienceofsynthesiscomesalivefromthepagesofthiswonderfultext,whichshouldearnitsrightfulplaceinthesyntheticchemist’slibraryandserveasaninspirationtotoday’sstudentstodiscover,inventandapplytheirownfuturenamedreactionsOurthanksarecertainlyduetoLászlóKürtiandBarbaraCzakóforasplendidcontributiontoourscienceKCNicolaouJanuary,TABLEOFCONTENTSSEARCHTEXTxiiPREFACEToday’sorganicchemistisfacedwiththechallengeofnavigatinghisorherwaythroughthevastbodyofliteraturegenerateddailyPapersandreviewarticlesarefullofscientificjargoninvolvingthedescriptionofmethods,reactionsandprocessesdefinedbythenamesoftheinventorsorbyawellacceptedphraseTheuseofsocalled“namedreactions”playsanimportantroleinorganicchemistryRecognizingthesenamedreactionsandunderstandingtheirscientificcontentisessentialforgraduatestudentsandpracticingorganicchemistsThisbookincludessomeofthemostfrequentlyusednamedreactionsinorganicsynthesisThereactionswerechosenonthebasisofimportanceandutilityinsyntheticorganicchemistryOurgoalistoprovidethereaderwithanintroductionthatincludesadetailedmechanismtoagivenreaction,andtopresentitsuseinrecentsyntheticexamplesThismanuscriptisnotatextbookintheclassicalsense:itdoesnotincludeexercisesorchaptersummariesHowever,bydescribingnamedorganicreactionsandmethodswithanextensivelistofleadingreferences,thebookiswellsuitedforindependentorclassroomstudyOnonehand,thecompiledinformationfortheseindispensablereactionscanbeusedforfindingimportantarticlesorreviewsonagivensubjectOntheotherhand,itcanalsoserveassupplementarymaterialforthestudyoforganicreactionmechanismsandsynthesisThisbookplacesgreatemphasisonthepresentationofthematerialDrawingsarepresentedaccuratelyandwithuniformityReactionsarelistedalphabeticallyandeachnamedreactionispresentedinaconvenienttwopagelayoutOnthefirstpage,abriefintroductionsummarizestheuseandimportanceofthereaction,includingreferencestooriginalliteratureandtoallmajorreviewspublishedaftertheprimaryreferenceWhenapplicable,leadingreferencestomodificationsandtheoreticalstudiesarealsogivenTheintroductionisfollowedbyageneralschemeofthereactionandbyadetailedmechanismdrawnusingafourcolorcode(red,blue,greenandblack)toensureeasyunderstandingThemechanismsalwaysreflectthelatestevidenceavailableforthegivenreactionIfthemechanismisunknownordebatable,referencestotherelevantstudiesareincludedThesecondpagecontainsorrecentsyntheticexamplesutilizingthepertinentnamedreactionInmostcasestheexamplesaretakenfromasyntheticsequenceleadingtothetotalsynthesisofanimportantmoleculeoranaturalproductSomeexamplesaretakenfromarticlesdescribingnovelmethodologiesThesyntheticsequencesaredrawnusingthefourcolorcode,andtheproceduresaredescribedbrieflyinsentencesIfaparticularnamedreactioninvolvesacomplexrearrangementortheformationofapolycyclicringsystem,numberingofthecarbonskeletonisincludedinadditiontothefourcolorcodeInthedepictedexamples,thereactionconditionsaswellastheratioofobservedisomers(ifany)andthereportedyieldsareshownThetargetofTABLEOFCONTENTSSEARCHTEXTxiiitheparticularsyntheticeffortisalsoillustratedwithcolorsindicatingwheretheintermediatesresideinthefinalproductTheapproachusedinthisbookisalsouniqueinthatitemphasizesthecleveruseofmanyreactionsthatmightotherwisehavebeenoverlookedThealmost,referencesareindexedattheendofthebookandincludethetitleofthecitedbook,booksection,chapter,journalorreviewarticleThetitlesofseminalpaperswritteninaforeignlanguageweretranslatedtoEnglishThenameoftheauthorofaspecificsyntheticexamplewaschosenastheonehavinganasteriskinthereferenceInordertomakethebookasuserfriendlyaspossible,wehaveincludedacomprehensivelistofabbreviationsusedinthetextordrawingsalongwiththestructureoftheprotectinggroupsandreagentsAlsoinanappendix,thenamedorganicreactionsaregroupedonthebasisoftheiruseincontemporarysynthesisThusthereadercanreadilyascertainwhichnamedorganicreactionseffectthesamesynthetictransformationsorwhichfunctionalgroupsareaffectedbytheuseofaparticularnamedreactionFinally,anindexisprovidedtoallowrapidaccesstodesiredinformationbasedonkeywordsfoundinthetextorthedrawingsLászlóKürtiBarbaraCzakóUniversityofPennsylvaniaPhiladelphia,PAJanuaryTABLEOFCONTENTSSEARCHTEXTxivIVEXPLANATIONOFTHEUSEOFCOLORSINTHESCHEMESANDTEXTThebookusesfourcolors(black,red,blue,andgreen)todepictthesyntheticandmechanisticschemesandhighlightcertainpartsofthetextInthe“Introduction”and“Mechanism”sectionsofthetext,thetitlenamedreactionprocess

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