A [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline

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dc.contributor.authorKaranfil A.
dc.contributor.authorBalta B.
dc.contributor.authorEskici M.
dc.date.accessioned2024-07-22T08:19:04Z
dc.date.available2024-07-22T08:19:04Z
dc.date.issued2012
dc.description.abstractRegioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding δ-amino-α,β-unsaturated esters after acidic hydrolysis. Hydrogenation of the unsaturated esters and subsequent thermal cyclization afforded the related alkyl substituted piperidine-2-ones. This approach represents a novel [3+3] cyclization strategy for the asymmetric synthesis of alkyl substituted piperidin-2-ones. Efficiency of the cyclization process is illustrated by a formal asymmetric synthesis of (S)-coniine from l-norvaline. © 2012 Elsevier Ltd. All rights reserved.
dc.identifier.DOI-ID10.1016/j.tet.2012.09.081
dc.identifier.issn14645416
dc.identifier.urihttp://akademikarsiv.cbu.edu.tr:4000/handle/123456789/17507
dc.language.isoEnglish
dc.subject1,2 cyclic sulfamidate derivative
dc.subjectalkyl group
dc.subjectamide
dc.subjectamino acid
dc.subjectconiine
dc.subjectester
dc.subjectlithium derivative
dc.subjectnorvaline
dc.subjectpiperidone derivative
dc.subjectunclassified drug
dc.subjectalkylation
dc.subjectannulation reaction
dc.subjectarticle
dc.subjectasymmetric synthesis
dc.subjectcyclization
dc.subjecthydrogenation
dc.subjecthydrolysis
dc.subjectnuclear Overhauser effect
dc.subjectpriority journal
dc.subjectproton nuclear magnetic resonance
dc.subjectring opening
dc.subjectstereochemistry
dc.subjectsubstitution reaction
dc.titleA [3+3] cyclization strategy for asymmetric synthesis of alkyl substituted piperidine-2-ones using 1,2-cyclic sulfamidates: A formal synthesis of (S)-coniine from l-norvaline
dc.typeArticle

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