Eskici, MKaranfil, AÖzer, MSSarikürkcü, C2024-07-182024-07-180040-4039http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/4127A 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.EnglishENANTIOSELECTIVE SYNTHESISSTEREOSELECTIVE-SYNTHESISASYMMETRIC-SYNTHESISLACTAM PRECURSORSSULFAMATE ESTERSFACILE ENTRYALPHADERIVATIVESACIDPROPIOLATEArticle