Alkyl 2-chloro-2-cyclopropylideneacetates - Remarkably versatile building blocks for organic synthesis

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dc.contributor.authorde Meijere, A.en
dc.contributor.authorKozhushkov, S. I.en
dc.contributor.authorHadjiarapoglou, L. P.en
dc.date.accessioned2015-11-24T16:45:14Z
dc.date.available2015-11-24T16:45:14Z
dc.identifier.issn0340-1022-
dc.identifier.urihttps://olympias.lib.uoi.gr/jspui/handle/123456789/8899
dc.rightsDefault Licence-
dc.subjectabsolute configurationen
dc.subjectaminesen
dc.subjectamino acidsen
dc.subjectcarbenesen
dc.subjectcascade reactionsen
dc.subject2-chloro-2-cyclopropylideneacetatesen
dc.subjectcombinatorial librariesen
dc.subjectcycloadditionsen
dc.subjectcyclobutenesen
dc.subjectcyclopropanesen
dc.subjectdiels-alder reactionsen
dc.subjectheterocyclesen
dc.subjectmichael additionsen
dc.subjectnitronesen
dc.subjectnucleophilic substitutionsen
dc.subjectpeptidomimeticsen
dc.subjectpalladium catalysisen
dc.subjectpolycyclesen
dc.subjectsolid phase synthesisen
dc.subjectspiro compoundsen
dc.subjectthiolsen
dc.subjectglycine cation equivalenten
dc.subjectoptically-active oxazolidinonesen
dc.subjectiminium ion rearrangementen
dc.subjectpotent bracken carcinogenen
dc.subjectaquilinum var latiusculumen
dc.subjectcyclopropane amino-acidsen
dc.subjectDNA cleaving activitiesen
dc.subjectacyl-coa dehydrogenaseen
dc.subjectbeta-lactam synthesisen
dc.subjectdiels-alder reactionsen
dc.titleAlkyl 2-chloro-2-cyclopropylideneacetates - Remarkably versatile building blocks for organic synthesisen
heal.abstractStrain in small rings has evolved as one of the principles used to control reactivity and chemoselectivity in transformations of organic compounds. The combination of small rings with multiple bonds and functional groups establishes composite functionalities which demonstrate unique multiple reactivity and thereby potentially high synthetic utility. This survey concentrates on a family of compounds which combines the chemistry of methylenecyclopropanes and that of electron-acceptor-activated alkenes, namely alkyl 2-chloro-2-cyclopropylideneacetates of types 1-3. This special feature makes the compounds 1-3 multifunctional as well as highly reactive, and thus extremely versatile building blocks for organic synthesis. Not only is the general synthetic access to methylenecyclopropanes 1-3 presented here, but particularly their rich chemistry as highly reactive Michael accepters, dienophiles, dipolarophiles and general cyclophiles which leads to a wide range of different types of functionally substituted cyclopropane derivatives, spirocyclopropane-annelated hetero- and carbocycles, mono- and oligocondensed cycles, natural and unnatural amino acids and peptidomimetics, and more. Finally, the first results obtained with polymer-bound substrates of types 1-3 in a combinatorial approach to libraries of potentially biologically active compounds are presented.en
heal.accesscampus-
heal.fullTextAvailabilityTRUE-
heal.identifier.secondary<Go to ISI>://000089035100004-
heal.identifier.secondaryhttps://docs.google.com/file/d/0BxfLht5wJUEIZjU5Zjg4ZDAtNzNhZC00NmQxLWFmOTYtMmZmM2FjY2ViZDQ3/edit?hl=en-
heal.journalNameSmall Ring Compounds in Organic Synthesis Vien
heal.journalTypepeer reviewed-
heal.languageen-
heal.publicationDate2000-
heal.recordProviderΠανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείαςel
heal.typejournalArticle-
heal.type.elΆρθρο Περιοδικούel
heal.type.enJournal articleen

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