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1、TetrahedronLetters56(2015)5397–5400ContentslistsavailableatScienceDirectTetrahedronLettersjournalhomepage:www.elsevier.com/locate/tetletAconvenientsynthesisofphosphonomethyla,b-unsaturatedc-lactamsa,baba,⇑b,⇑AbderrahmenAbdelli,MohamedLotfiEfrit,AnneGaucher,HediM’rabet,DamienPrimaU
2、niversitédeTunisElManar,FacultédesSciencesdeTunis,LaboratoiredeSynthèseOrganiqueetHétérocyclique,2092Tunis,TunisiabUniversitédeVersaillesSaintQuentin-en-Yvelines,InstitutLavoisierdeVersailles-UMRCNRS8180,45avenuedesEtats-Unis,78035Versailles,FrancearticleinfoabstractArticlehistor
3、y:Aversatileaccesstodiverselysubstituteda,b-unsaturatedc-lactamsisdescribedusingacommonReceived6July2015allylphosphonateprecursor.Theconstructionofthec-lactammotiveisbasedontwostepsincludingaRevised28July2015keysequentialone-potMichaeladdition–Nefsequencethatallowsthepreparationo
4、fketo-esterinterme-Accepted31July2015diates.Ourmethodologyallowedtheselectiveinstallationofvariousalkyl,cycloalkylandarylsub-Availableonline3August2015stituentsaswellasavaluablephosphonomethylfragmentatpositions1and3oftheheterocycle.Ó2015ElsevierLtd.Allrightsreserved.Keywords:Ket
5、o-estersc-LactamsAllylphosphonatesMichaeladditionNefreactionIntroductiondihydropyrrol-2-onederivatives(Fig.2).Ourstrategyisbasedontheconstructionofthec-lactamscaffoldfromc-ketoesterinter-a,b-Unsaturatedc-lactamsalsocalleddihydropyrrol-2-onesmediatesobtainedfromallylphosphonatesas
6、keyprecursors.representasubclassofthemoregeneralc-lactamfamily.ThewideWefirststartedtoexaminethetransformationofallylphospho-panelofpharmaceuticalandbiologicalactivitiesdisplayedbysuchnatesintoc-ketoesters.Atafirstglance,weenvisionedtwoinde-1aza-heterocyclesfocusedtheinterestofthes
7、cientificcommunity.pendentstepsimplyingfirstMichaeltypeadditionofaliphatic211SelectedexamplesdepictedinFigure1,showherbicidal1andnitrocompoundstotheallylgroupfollowedbyaNefreaction3antitumor2activitiesaswellasantibacterialandcytotoxicprop-toaffordtheexpectedphosphonomethylc-ketoest
8、ers.4erties5(Fig.1).Theheterocyclicpatte
