Allenamides_ A Powerful and Versatile Building Block in Organic Synthesis

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1、Reviewpubs.acs.org/CRAllenamides:APowerfulandVersatileBuildingBlockinOrganicSynthesis†††,‡,†TingLu,ZhenjieLu,Zhi-XiongMa,YuZhang,*andRichardP.Hsung*†DivisionofPharmaceuticalSciences,SchoolofPharmacy,UniversityofWisconsin,Madison,Wisconsin53705,UnitedStates‡Discove

2、ryResearch,DowAgroSciencesLLC,Indianapolis,Indiana46268,UnitedStates3.6.3.[2+2+1]Cycloadditions48883.6.4.[3+2]Cycloadditions48883.6.5.[4+2]Cycloadditions48903.6.6.[3+3]FormalCycloadditions48933.6.7.[4+3]Cycloadditions48943.7.TandemCascadesviaIsomerizations48963.7.

3、1.α-Isomerizations48963.7.2.γ-Isomerizations48974.NaturalProductSynthesis4898CONTENTS5.MostRecentDevelopment49006.Conclusion49001.Introduction4862AuthorInformation49002.Preparation4864CorrespondingAuthor49002.1.HistoricalExamples4864Notes49002.2.SigmatropicRearran

4、gements4864Biographies49002.3.Base-InducedIsomerizations4866References49012.3.1.CyclicPropargylAmides48662.3.2.AcyclicPropargylAmides48682.4.Eliminations48681.INTRODUCTION2.5.Amino-Cyclizations4869Inthepastfourdecades,alleneshaveprogressivelyrisenfrom2.6.Trost−Hsu

5、ngN-Allenylations4870anunenviablestatusofbeingastructuralcuriositytobecoming2.7.Suzuki−MiyauraCross-Coupling4871oneofthemostpowerfulandversatilesyntheticbuildingblocks3.ReactionsofAllenamides48711−3inorganicsynthesis.Althoughthefocalthemeofthis3.1.Deprotonations48

6、71Reviewiscenteredonthechemistryofallenamides,aproper3.1.1.α-Deprotonations4871introductionwouldneedtocommencewithallenamines.3.1.2.γ-Deprotonations48714Allenamidesarefunctionallyderivedfromallenamines,which3.2.AdditionReactions48715alongwithstructurallyrelatedsys

7、temssuchasallenolethers3.2.1.Hydroalkoxylations48716andallenylsulfidescanbeclassifiedasheteroatom-substituted3.2.2.Hydro−Hydroxyalkylations4872allenes.Allenamineshavebeenknownformorethan40years3.2.3.Hydroaminations4872sincethefirstdocumentationoftheirpreparationsand3

8、.2.4.Hydroarylations48747characterizationsin1968byViehe.Itisnoteworthythat3.2.5.Hydroalkenylations4875Viehewasatthetimedevelopingabased-catalyzedisomer-