Please use this identifier to cite or link to this item: http://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2714
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dc.contributor.authorEskici, Mustafa-
dc.contributor.authorKaranfil, Abdullah-
dc.date.accessioned2022-08-17T07:15:47Z-
dc.date.available2022-08-17T07:15:47Z-
dc.date.issued2019-
dc.identifier.urihttp://doi.org/10.1016/j.tet.2019.01.030-
dc.identifier.urihttp://earsiv.odu.edu.tr:8080/xmlui/handle/11489/2714-
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. (C) 2019 Elsevier Ltd. All rights reserved.en_US
dc.language.isoengen_US
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLANDen_US
dc.relation.isversionof10.1016/j.tet.2019.01.030en_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subject1,2-Cyclic sulfamidates; Acetylide; Ketal; Stereoselective synthesis; Cyclization; Piperidinesen_US
dc.titleStereoselective synthesis of cis-2,6-disubstituted piperidines from 1,2-cyclic sulfamidatesen_US
dc.typearticleen_US
dc.relation.journalTETRAHEDRONen_US
dc.contributor.departmentOrdu Üniversitesien_US
dc.contributor.authorID0000-0003-2948-4216en_US
dc.identifier.volume75en_US
dc.identifier.issue9en_US
dc.identifier.startpage1214en_US
dc.identifier.endpage1222en_US
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