Browsing by Author "Sarikürkcü, C"

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    Reactivity of cyclic sulfamidates towards lithium acetylides: synthesis of alkynylated amines
    Eskici, M; Karanfil, A; Özer, MS; Sarikürkcü, C
    A 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.