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.accessioned2024-07-18T11:48:56Z
dc.date.available2024-07-18T11:48:56Z
dc.description.abstractRegioselective ring-opening reactions of a set of representative 1,2-cyclic sulfamidates with lithium triethylorthopropiolate proceeded efficiently to deliver the corresponding delta-amino-alpha,beta-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. (c) 2012 Elsevier Ltd. All rights reserved.
dc.identifier.issn0040-4020
dc.identifier.urihttp://akademikarsiv.cbu.edu.tr:4000/handle/123456789/3645
dc.language.isoEnglish
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.subjectGLYCOSYL AMINO-ACIDS
dc.subjectENANTIOSELECTIVE SYNTHESIS
dc.subjectSTEREOSELECTIVE-SYNTHESIS
dc.subjectEFFICIENT SYNTHESIS
dc.subjectLACTAM PRECURSORS
dc.subjectCYCLIC SULFAMATE
dc.subjectFACILE ENTRY
dc.subjectALPHA
dc.subjectREACTIVITY
dc.subjectDERIVATIVES
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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