Reactivity of cyclic sulfamidates towards lithium acetylides: synthesis of alkynylated amines

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dc.contributor.authorEskici, M
dc.contributor.authorKaranfil, A
dc.contributor.authorÖzer, MS
dc.contributor.authorSarikürkcü, C
dc.date.accessioned2024-07-18T11:49:34Z
dc.date.available2024-07-18T11:49:34Z
dc.description.abstractA synthetically useful level of reactivity of cyclic sulfamidates toward acetylides is described. Ring-opening reactions of a structurally diverse set of 1,2- and 1,3-cyclic sulfamidates with a range of lithium acetylides from aliphatic, cyclic, aromatic, heteroaromatic, and functionalized alkynes proceed smoothly in a regioselective manner to give the corresponding N-sulfate intermediates. Hydrolysis of these intermediates under acidic conditions furnishes the alkynylated amines in yields ranging from 29% to 98%. The scope of the acetylenic substitution reaction with the structural variations in both the cyclic sulfamidates and alkynes is briefly examined. (C) 2011 Elsevier Ltd. All rights reserved.
dc.identifier.issn0040-4039
dc.identifier.urihttp://akademikarsiv.cbu.edu.tr:4000/handle/123456789/4127
dc.language.isoEnglish
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.subjectENANTIOSELECTIVE SYNTHESIS
dc.subjectSTEREOSELECTIVE-SYNTHESIS
dc.subjectASYMMETRIC-SYNTHESIS
dc.subjectLACTAM PRECURSORS
dc.subjectSULFAMATE ESTERS
dc.subjectFACILE ENTRY
dc.subjectALPHA
dc.subjectDERIVATIVES
dc.subjectACID
dc.subjectPROPIOLATE
dc.titleReactivity of cyclic sulfamidates towards lithium acetylides: synthesis of alkynylated amines
dc.typeArticle

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