Browsing by Author "Sarikürkcü C."

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    Reactivity of cyclic sulfamidates towards lithium acetylides: Synthesis of alkynylated amines
    (2011) Eskici M.; Karanfil A.; Özer M.S.; 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. © 2011 Elsevier Ltd. All rights reserved.