Asymmetric Ene Reactions in Organic Synthesis.pdf

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1、chsm.Rev.1992,92,1021-10501021AsymmetricEneReactionsinOrganicSynthesisKoichiMikami’andMasakiShimizuDspa”ofC?”fcalTsdnokgy.T&yoInsthie01Tsdnokgy.Megupku.T&yo152.JapanRecslvsdDeosmber2,1991pevlsedManuscr@tReceWMay4,1992)ContentsI.Introduction102111.ScopeandLimitations1022A.CarbonyC

2、EneReactions10228.Olefin-€neReactions1024C.Acatylene-EneReactions1024D.AlienesasEnophiiesorEnes1025111.MechanisticAspects1025A.ThermalvsLewisAcibPromoted1025ReactionsB.ContinuumfromConcartedtoCatbnlc1028MechanismC.SueReactionsandByproducts1028IV.StereochemicalAspects1028KoichiMka

3、miwasbornin1953andreceivedhisB.S.degreeandA.Transnion-StateModels1028Ph.D.fromTokyoInstituteofTechnologywnhTakeshiNakal.HeB.Regloselection1028JoinedthefacuityofTITin1982asanAssistantProfessor.In1987.hewaspromotedtoAssociateProfessor.From1982toC.OlefinicDlastereoselection10301983h

4、ewasapostdoctraifallowattheYaleUniversitywkhFre-D.InternalAsymmetricInduction:Endo1031derlckE.Ziegkn.HismajorrasearchinterestsarethedevelopmentsPreference?ofnewmemodsandsbat~sfworganicsynmesis,theasymmeficE.RelativeAsymmetricInductbn1033cataiysisofsyntheticorganicreactions.andthe

5、irapplicationtonaturalproductsynthesisF.RemoteAsymmemcInduction10360.AsymmetricTransfer1036H.AsymmetricCatalysis1038I.AsymmetricDesymmemzatbn1039J.AsymmetricAmplification:PosWe1039NonlinearEffectV.EneCyclizations1041A.DlastereofaciaiSelection1042B.IntraannularDiastereoselectbn104

6、3C.ExtraannularDlastereoselection1043D.OlefinicDiastereoselection1044E.AsymmetricCatalysls1045F.AsymmetricDesymmemzation1045G.Metallo-EneReaction1045MasakiShimlzuwasborninTokyo,Japan,in1965.HegraduatedfromTokyoInstituteofTechnologyin1969.wherehehasnowI.IntroducllonJoinedthePh.D.p

7、rogramunderthedirectionofKoichiMikami.C-HbondactivationandC-Cbondformationarethecluestosyntheticexploitationinorganicsynthesis.enophile)toformtwou-bondswithmigrationoftheInprinciple,theenereaction,whichconvertsreadilyr-bond.Theenereactionismechanisticallyrelatedtoavailablealkenes

8、withactivationofanallylicC-Hbondthemuchb