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1、pubs.acs.org/jocProtecting-Group-FreeSynthesisofAmines:SynthesisofPrimaryAminesfromAldehydesviaReductiveAmination?,??,??,?EmmaM.Dangerfield,CatherineH.Plunkett,AnnaL.Win-Mason,,?,?BridgetL.Stocker,*andMattieS.M.Timmer*??MalaghanInstituteofMedicalResearch,POBox70
2、60,Wellington,NewZealand,andSchoolofChemicalandPhysicalSciences,VictoriaUniversityofWellington,POBox600,Wellington,NewZealandbstocker@malaghan.org.nz;mattie.timmer@vuw.ac.nzReceivedJanuary4,2010Newmethodologyfortheprotecting-group-freesynthesisofprimaryaminesisp
3、resented.Byoptimi-zingthemetalhydride/ammoniamediatedreductiveaminationofaldehydesandhemiacetals,primaryamineswereselectivelypreparedwithnoorminimalformationoftheusualsecondaryandtertiaryaminebyproduct.Themethodologywasperformedonarangeoffunctionalizedaldehydesu
4、bstrates,includinginsituformedaldehydesfromaVasellareaction.Thesereductiveaminationconditionsprovideavaluablesynthetictoolfortheselectiveproductionofprimaryaminesinfewersteps,ingoodyields,andwithouttheuseofprotectinggroups.IntroductionTraditionally,protectinggro
5、upshavebeenusedwhenpre-paringprimaryaminesviametalhydridereductiveamina-Aminesareanimportantclassofcompoundsfoundin7-9tion.Protectinggroupshaveanimportantroleinorganicmanynaturalproducts,pharmaceuticals,andothervaluable101,2synthesis,yettheirincorporationintoasy
6、ntheticroutehasorganicmoleculesincludingdyesandagrochemicals.anumberofdisadvantagesincludinganincreaseinthetotalAlthoughtherearemanysynthetictransformationsthatcan1numberofstepsinthesequence(protectionanddeprotectionbeusedtoprepareamines,methodologyfortheselecti
7、ve11steps)anddecreasesinatom-economy.Protectinggroupssynthesisofprimaryaminesismorelimited.Ofthese,reduc-3-5alsoaddfunctionalgroupsandstructuralcomplexitytoativeaminationsareparticularlyimportant,andreactions4molecule,whichcanhavedetrimentaleffectsonorthogon-uti
8、lizingmolecularhydrogenasthereducingagentinthe5,6alityandreactivity.Inmetalhydridereductiveaminations,presenceofasuitablecatalysthaveprovenveryeffective.theuseofprote
