Radical [3 2] Annulation of

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1、ORGANICLETTERSRadical[3+2]Annulationof2001Vol.3,No.17N-Allyl-N-chlorotosylamidewithAlkenes2709-2711viaAtom-TransferProcessTakayukiTsuritani,HiroshiShinokubo,andKoichiroOshima*DepartmentofMaterialChemistry,GraduateSchoolofEngineering,KyotoUniVersity,Kyoto606-8501,Japanoshima@fm1.kuic.kyoto-

2、u.ac.jpReceivedJune20,2001ABSTRACTAradical[3+2]annulationreactionwithanN-centeredradicalhasbeendeveloped.ThereactionofalkeneswithN-allyl-N-chlorotosylamideyieldsthecorrespondingpyrrolidinederivativesingoodyieldsinthepresenceofEt3Basaradicalinitiator.Theuseofradicalspeciesinorganicsynthesis

3、hasincreasedradicalshavebeenreportedsofar.5Hereinwewishtoreportdramaticallyinthepasttwodecades.1Duringthoseyears,theintermolecularradicaladditionofN-allylamidylradicalsinter-andintramolecularradicaladditionreactionsthattowardalkenestoformpyrrolidinederivatives,[3+2]exploitcarbon-centeredra

4、dicalspecieshavefoundwide-annulationproducts.spreadapplication.2Recently,intramolecularcyclizationofIngeneral,annulationisamoreconvergentstrategythanN-centeredradicalshasemergedasanefficientmethodforintramolecularcyclization,andhenceradicalannulationtheconstructionofnitrogenheterocycles.3,

5、4However,onlybasedonanintermolecularadditioncanbeanexpeditiousfewexamplesoftheintermolecularadditionofN-centeredstrategyforconstructingcycliccompounds.6Scheme1(1)(a)RadicalsinOrganicSynthesis;Renaud,P.,Sibi,M.P.,Eds.;Wiley-VCH:Weinheim,2001.(b)Curran,D.P.;Porter,N.A.;Giese,B.Stereochemistr

6、yofRadicalReactions;VCHVerlagsgesellschaftmbH.:Scheme1Weinheim,1996.(c)Giese,B.;Kopping,B.;GoÈbel,T.;Dickhaut,J.;Thoma,G.;Kulicke,K.J.;Trach,F.Org.React.1996,48,301.(d)Curran,D.P.InComprehensiVeOrganicSynthesis;Trost,B.M.,Fleming,I.,Eds.;PergamonPress:Oxford1991;Vol.4,Chapter4.2,p779.(e)Mc

7、Carroll,A.J.;Walton,J.C.Angew.Chem.,Int.Ed.2001,40,2224.(2)Forapplicationintotalsyntheses,see:(a)Jasperse,C.P.;Curran,D.P.;Fevig,T.L.Chem.ReV.1991,91,1237.(b)Banik,B.K.Curr.Org.Chem.1999,3,469.(3)Forrecentexamples,see:(a)Uchiyama,K.;Hayashi,Y.;Narasaka,K.Tetra