Stereoselective Formation of Amines PDF
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Topics in Current Chemistry 343 Wei Li Xumu Zhang Editors Stereoselective Formation of Amines 343 Topics in Current Chemistry EditorialBoard: K.N.Houk,LosAngeles,CA,USA C.A.Hunter,Sheffield,UK M.J.Krische,Austin,TX,USA J.-M.Lehn,Strasbourg,France S.V.Ley,Cambridge,UK M.Olivucci,Siena,Italy J.Thiem,Hamburg,Germany M.Venturi,Bologna,Italy C.-H.Wong,Taipei,Taiwan H.N.C.Wong,Shatin,HongKong Forfurthervolumes: http://www.springer.com/series/128 Aims and Scope TheseriesTopicsinCurrentChemistry presentscriticalreviews ofthepresent and futuretrendsinmodernchemicalresearch.Thescopeofcoverageincludesallareasof chemical science including the interfaces with related disciplines such as biology, medicineandmaterialsscience. Thegoalofeachthematicvolumeistogivethenon-specialistreader,whetherat theuniversityorinindustry,acomprehensiveoverviewofanareawherenewinsights areemergingthatareofinteresttolargerscientificaudience. Thuseachreviewwithinthevolumecriticallysurveysoneaspectofthattopicand placesitwithinthecontextofthevolumeasawhole.Themostsignificantdevelop- mentsofthelast5to10yearsshouldbepresented.Adescriptionofthelaboratory procedures involved is often useful to the reader. The coverage should not be exhaustiveindata,butshouldratherbeconceptual,concentratingonthemethodolog- icalthinkingthatwill allowthenon-specialistreaderto understandtheinformation presented. Discussionofpossiblefutureresearchdirectionsintheareaiswelcome. Reviewarticlesfortheindividualvolumesareinvitedbythevolumeeditors. Readership:researchchemistsatuniversitiesorinindustry,graduatestudents. Wei Li Xumu Zhang l Editors Stereoselective Formation of Amines With contributions by (cid:1) (cid:1) (cid:1) (cid:1) A.B. Charette Q.-H. Fan G.K. Friestad Y.-M. He (cid:1) (cid:1) (cid:1) (cid:1) K.C. Hultzsch W. Li V. Lindsay A.J. Nawara-Hultzsch (cid:1) (cid:1) (cid:1) (cid:1) A.L. Reznichenko F.-T. Song C. Wang J. Xiao (cid:1) (cid:1) J.-H. Xie X. Zhang Q.-L. Zhou Editors WeiLi XumuZhang InstituteofChemicalBiologyand DepartmentofChemistryandChemical DrugDiscovery Biology,DepartmentofMedicinal StonyBrookUniversity Chemistry StonyBrook,NY Rutgers,TheStateUniversityofNewJersey USA Piscataway,NJ USA ISSN0340-1022 ISSN1436-5049(electronic) ISBN978-3-642-53928-2 ISBN978-3-642-53929-9(eBook) DOI10.1007/978-3-642-53929-9 SpringerHeidelbergNewYorkDordrechtLondon LibraryofCongressControlNumber:2014933584 #Springer-VerlagBerlinHeidelberg2014 Thisworkissubjecttocopyright.AllrightsarereservedbythePublisher,whetherthewholeorpartof the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation,broadcasting,reproductiononmicrofilmsorinanyotherphysicalway,andtransmissionor informationstorageandretrieval,electronicadaptation,computersoftware,orbysimilarordissimilar methodologynowknownorhereafterdeveloped.Exemptedfromthislegalreservationarebriefexcerpts inconnectionwithreviewsorscholarlyanalysisormaterialsuppliedspecificallyforthepurposeofbeing enteredandexecutedonacomputersystem,forexclusiveusebythepurchaserofthework.Duplication ofthispublicationorpartsthereofispermittedonlyundertheprovisionsoftheCopyrightLawofthe Publisher’s location, in its current version, and permission for use must always be obtained from Springer.PermissionsforusemaybeobtainedthroughRightsLinkattheCopyrightClearanceCenter. ViolationsareliabletoprosecutionundertherespectiveCopyrightLaw. The use of general descriptive names, registered names, trademarks, service marks, etc. in this publicationdoesnotimply,evenintheabsenceofaspecificstatement,thatsuchnamesareexempt fromtherelevantprotectivelawsandregulationsandthereforefreeforgeneraluse. While the advice and information in this book are believed to be true and accurate at the date of publication,neithertheauthorsnortheeditorsnorthepublishercanacceptanylegalresponsibilityfor anyerrorsoromissionsthatmaybemade.Thepublishermakesnowarranty,expressorimplied,with respecttothematerialcontainedherein. Printedonacid-freepaper SpringerispartofSpringerScience+BusinessMedia(www.springer.com) Preface Chiral amines are widespread structural units in chiral auxiliaries and bioactive molecules, such as agrochemicals and active pharmaceutical ingredients. Histori- cally, there has been interest in producing chiral amines, and such interest has promoted a variety of methodologies to synthesize chiral amines – ideally in a singleisomer.Organicchemists,particularlyorganometallicchemistryresearchers, have made tremendous strides toward developing novel chemical technologies to tackle the long-standing challenge of producing chiral amines via operationally simple,economic,andhighlystereoselectivemethods. Despite the fact that chiral amines have been recognized for their importance datingbackseveraldecades,thetoplong-existingchallengesonthelisthavebeen narrowsubstratescope,relativelylowturnovernumberscausedbycatalystinhibi- tion/deactivation by amine products, and the necessity of protecting groups. Fol- lowingtheseminalstudiesinthe1990s,inmorerecentyearsafast-growingbodyof creativeresearchhasemerged,yieldingversatileandpowerfultransformationsfor introducing chiral amines stereoselectively. This array of methods has made this once challenging ambition easier to realize. These new methods have drastically shortened possible routes to a given natural product or pharmaceutical drug con- taining a chiral amine moiety. The increasingly versatile development of new methodswillbeimplementedintonovelsyntheticstrategiesinthefuture. Thisvolumecontainsvaluableandinsightfulcontributionsfromseveralleading experts in this field, and the reviews within collectively provide an overview of a diverse set of valuable approaches as well as their implementation toward natural product and pharmaceutical synthesis. Asymmetric free radical addition to imino compounds is addressed in the first chapter, mainly dealing with the use of chiral hydrazonesasradicalacceptors.Thesecondchapterpresentsanin-depthreviewof the nucleophilic addition of unstabilized carbanions to azomethine derivatives. With a biased emphasis on asymmetric hydrogenation methodology, the subsequentthreechaptersprovide anin-depthoverview ofthe mostpowerfuland straightforward asymmetric transformations using hydrogen as the reducing re- agent on three main substrate categories: enamide/enamine, imine, and v vi Preface heteroaromatics,respectively.Acomprehensivecontributiononasymmetrichydro- amination displays solid examples of efficient catalyst systems that underline the usefulnessofthedirectadditionofN–Hbondsacrossanunsaturatedcarbon–carbon bondtoformalchiralamines.Thefinalsectioncoverscurrentmethodsandrecent advances in asymmetric reductive amination by hydrogenation, transfer hydroge- nation, organocatalytic reduction, and biocatalytic reduction, as a review of the state-of-the-artmethodofasymmetricreductiveamination.Unfortunately,wewere unabletoincludeotherimportanttopicslikeenantioselectiveC–Hamination,and recently-emerging enzymatic approaches via dynamic kinetic resolution or trans- aminasetechnologyaschaptersinthisshortvolume. Wewouldliketoexpressoursinceregratitudetothosewhocontributedtothis volume.Weappreciatetheirvaluabletimeandeffortandexpectthattheirviewson futureresearchtrendswillbeusefultoallresearchersinthefield. Rutgers,TheStateUniversityofNewJersey,Piscataway,NJ,USA XumuZhang StonyBrookUniversity,StonyBrook,NY,USA WeiLi September2013 Contents ControlofAsymmetryintheRadicalAdditionApproachtoChiral AmineSynthesis ................................................................ 1 GregoryK.Friestad StereoselectiveFormationofAminesbyNucleophilicAddition toAzomethineDerivatives .................................................... 33 Andre´ B.CharetteandVincentLindsay TransitionMetal-CatalyzedEnantioselectiveHydrogenation ofEnamidesandEnamines ................................................... 75 Qi-LinZhouandJian-HuaXie AsymmetricHydrogenationofImines ...................................... 103 WeiLiandXumuZhang AdvancesinTransitionMetal-CatalyzedAsymmetricHydrogenation ofHeteroaromaticCompounds ............................................. 145 Yan-MeiHe,Feng-TaoSong,andQing-HuaFan AsymmetricHydroamination ............................................... 191 AlexanderL.Reznichenko,AgnieszkaJ.Nawara-Hultzsch, andKaiC.Hultzsch AsymmetricReductiveAmination .......................................... 261 ChaoWangandJianliangXiao Index .......................................................................... 283 vii TopCurrChem(2014)343:1–32 DOI:10.1007/128_2013_481 #Springer-VerlagBerlinHeidelberg2013 Publishedonline:28September2013 Control of Asymmetry in the Radical Addition Approach to Chiral Amine Synthesis GregoryK.Friestad Abstract The state-of-the-science in asymmetric free radical additions to imino compounds is presented, beginning with an overview of methods involving stereocontrol by various chiral auxiliary approaches. Chiral N-acylhydrazones are discussedwithrespecttotheiruseasradicalacceptorsforMn-mediatedintermolecular additions,fromdesigntoscopesurveystoapplicationstobiologicallyactivetargets. A variety of aldehydes and ketones serve as viable precursors for the chiral hydrazones,andavarietyofalkyliodidesmaybeemployedasradicalprecursors,as discussed in a critical review of the functional group compatibility of the reaction. Applications to amino acid and alkaloid synthesis are presented to illustrate the syntheticpotentialoftheseversatilestereocontrolledcarbon–carbonbondconstruction reactions.Asymmetriccatalysisisdiscussed,fromseminalworkonthestereocontrol of radical addition to imino compounds by non-covalent interactions with stoichio- metricamountsofcatalysts,tomorerecentexamplesdemonstratingcatalystturnover. Keywords Asymmetricsynthesis(cid:1)Hydrazones(cid:1)Imines(cid:1)Oximeethers(cid:1)Radical reactions Contents 1 BackgroundandIntroduction................................................................ 2 2 IntermolecularRadicalAdditiontoChiralN-Acylhydrazones............................. 3 2.1 UseofChiralAuxiliariesinRadicalAdditionstoIminoCompounds............... 3 2.2 DesignofChiralN-Acylhydrazones................................................... 5 2.3 PreparationandInitialReactivityStudiesofChiralN-Acylhydrazones............. 6 2.4 Manganese-MediatedRadicalAddition:DiscoveryandMethodDevelopment..... 10 2.5 HybridRadical–IonicAnnulation..................................................... 12 2.6 ApplicationsinAminoAcidSynthesis................................................ 16 G.K.Friestad(*) DepartmentofChemistry,UniversityofIowa,IowaCity,IA52242,USA e-mail:[email protected] 2 G.K.Friestad 2.7 ConsiderationsforSynthesisDesignUsingMn-MediatedRadicalAddition........ 21 3 AsymmetricCatalysisofRadicalAddition................................................. 24 4 Summary...................................................................................... 28 References........................................................................................ 29 1 Background and Introduction Chiral α-branched amine functionalities are present in a wide range of bioactive synthetictargets,bothnaturalandunnatural.Accordingly,avarietyofmethodsfor asymmetricaminesynthesishavebeendevelopedoverrecentyears,manyofwhich involve carbon–carbon bond constructions by addition to the C¼N bond of car- bonyliminoderivatives,representedintheretrosyntheticdirectioninFig.1(Recent reviews:see[1–10]). As is typical in most synthetic chemistry, methods accrue higher impact if they offer configurational control under mild conditions compatible with a range of spectator functional groups. Unfortunately, many methods involving nucleophilic additionsofcarbanion-typereagentstoC¼Nbondshavelimitedcompatibilitywith electrophilicoracidicfunctionality,ormayresultincompetingdeprotonationatthe imine α-carbon due to the basicity of the organometallic reagent (For examples of aza-enolizationofiminocompoundsbyorganometallicreagentssee[11–14]).These limitationshavespurredthedevelopmentoffreeradicaladditions(Reviewsoffree radical reactions in synthesis: see [15–21]) to imino compounds (Fig. 2) as a C–C bond construction approach to chiral amines under mild conditions, offering a valuable complement to organometallic additions and expanding the scope of this α-C–C retrosynthetic disconnection (Reviews of radical additions to imines and relatedacceptors:see[2,22–25]). Seeking to probe the improved versatility which might be associated with the radical addition approach, we initiated a program to develop a variety of radical additions to imino compounds [26]. In the process we introduced several new modesofstereocontrolusinghydrazonesastheC ¼ Nradicalacceptorfunctionality. Iminocompoundshavebeenextensivelyusedforcyclizations[27],andinitiallywe built upon this foundation by introducing a temporary tethering approach [28–34] which has been effective in establishing relative configuration in a predictable diastereoselective fashion via reactions of α-hydroxyaldehyde hydrazones(Reviews oftemporarytethers:see[35–43]).Inthisreviewwewillfocusontheintermolecular variant of the reaction, for which we have introduced methodology to build chiral amines from achiral precursors using chiral auxiliaries or chiral catalysts for stereocontrol[44];thedesignandexperimentalevaluationofthesestrategieswillbe describedalongwithsyntheticapplications.
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