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1、Tetrahedron:Asymmetry24(2013)568–574ContentslistsavailableatSciVerseScienceDirectTetrahedron:Asymmetryjournalhomepage:www.elsevier.com/locate/tetasyMethodsforthesynthesisofchiralsulfurheterocyclesandtheirapplicationintheasymmetricBaylis–HillmanreactionsMariappa
2、nPeriasamy⇑,RamaniGurubrahamam,GopalP.MuthukumaragopalSchoolofChemistry,UniversityofHyderabad,CentralUniversityPO,Hyderabad500046,IndiaarticleinfoabstractArticlehistory:Enantiomericallypure(2S,6S)-2,6-diphenyltetrahydro-2H-thiopyran,(2S)-2-phenyltetrahydrothio-
3、Received13February2013phene,and(2S)-2-phenyltetrahydro-2H-thiopyranwerepreparedin70–72%yieldsandwith86–99%Accepted28March2013eeviacyclizationofthecorrespondingdimesylateinanS2cyclizationreactionusingsodiumsulfideNnonahydrate.Theresultsontheapplicationofvariousch
4、iralsulfidesinasymmetricBaylis–Hillmanreac-tionsarealsodescribed.DedicatedtoProfessorD.BasavaiahforhisÓ2013ElsevierLtd.Allrightsreserved.contributiontothedevelopmentoftheBaylis–Hillmanreaction1.Introduction1dingoodyield(90%)with97%ee(enrichedto99%bycrystalliza-t
5、ion).Thedimesylateofchiraldiol1dwaspreparedusingMsCl/9Chiralmoleculescontainingsulfidemoietiesareusefulforvar-NEt3whichuponcyclizationusingNa2S9H2OinDMSOaffordediousasymmetrictransformationssuchasasymmetricepoxida-theC2-symmetricchiralsulfide1with72%yieldand99%e
6、e.12tions,aziridinationofimines,catalyticasymmetricTheabsolutestereochemistryofchiralsulfide1wasconfirmed3cyclopropanationofelectrondeficientalkenes,andthesynthesistobe(2S,6S)bysinglecrystalX-raystructuralanalysisofitssul-4ofchiralalcoholsandaminesfromorganoborane
7、s.Theyarealsofone1eobtainedafterm-CPBAoxidation(Scheme1).TheORTEP5usefulinenantioselectivecascadereactionsandasymmetricBay-diagramofsulfone1eisshowninFigure2.6lis–Hillmanreactions.ChiralsulfidesareusefulinthesynthesisofRecently,theC1-symmetricchiral(2S)-phenylte
8、trahydrothi-biologicallyactivemotifssuchasiso-agatharesinol,swainsonine,ophene2hasbeenpreparedviatheCBSreductionofaketophosp-thesidechainoftaxol,andtheanti-inflammatoryagents
