Stereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates

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dc.contributor.authorEskici M.
dc.contributor.authorKaranfil A.
dc.date.accessioned2024-07-22T08:08:44Z
dc.date.available2024-07-22T08:08:44Z
dc.date.issued2019
dc.description.abstractDiastereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates is described. Regioselective ring-opening reactions of 1,2-cyclic sulfamidates derived from L-phenylalanine, alanine, valine, norvaline with the ketal protected acetylide with a phenyl substituent proceed smoothly to form the N-sulfamate intermediates which on acidic hydrolysis give alkynylated amines with the ketal group intact. Hydrogenation of the alkynylated amines, debenzylation, ketal deprotection, subsequent cyclization (of aminoketones) and stereoselective hydrogenation of the cyclic iminium ion intermediates afford the corresponding cis-2,6-disubstituted piperidines in high diastereoselectivity (98% ≥ d.e.) with good chemical yields (68–86%). The present approach provides a novel route for the stereoselective synthesis of cis-2,6-disubstituted piperidines. © 2019 Elsevier Ltd
dc.identifier.DOI-ID10.1016/j.tet.2019.01.030
dc.identifier.issn00404020
dc.identifier.urihttp://akademikarsiv.cbu.edu.tr:4000/handle/123456789/14511
dc.language.isoEnglish
dc.publisherElsevier Ltd
dc.subjectacetal
dc.subjectalanine
dc.subjectamine
dc.subjectaminoketone
dc.subjectbenzene derivative
dc.subjectnorvaline
dc.subjectphenylalanine
dc.subjectpiperidine derivative
dc.subjectsulfamide derivative
dc.subjectvaline
dc.subjectacidity
dc.subjectalkynylation
dc.subjectArticle
dc.subjectcarbon nuclear magnetic resonance
dc.subjectchemical structure
dc.subjectdebenzylation
dc.subjecthydrogenation
dc.subjecthydrolysis
dc.subjectliquid chromatography-mass spectrometry
dc.subjectpriority journal
dc.subjectproton nuclear magnetic resonance
dc.subjectregioselectivity
dc.subjectring opening
dc.subjectstereoselectivity
dc.subjectsynthesis
dc.titleStereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidates
dc.typeArticle

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