Karanfil A.Eskici M.2024-07-222024-07-22201700397911http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/15195Practical and economical synthesis of synthetically valuable 3,3,3-triethoxypropyne, ketal protected phenyl and methyl substituents prop-2-ynones is described. Bromination and subsequent 18-crown-6 catalyzed elimination of triethylorthoacrylate and ketal protected terminal alkenes with methyl and phenyl substituent which are inturn readily available from triethylorthopropionate, 3-chlorobutan-2-one and propiophenone afforded multigram quantities (>10 g) of corresponding functionalized terminal alkynes. Exploration of the synthetic utility of these alkynes is also demonstrated by the acetylenic substitution of the phenylalaninol derived 1,2-cyclic sulfamidate to deliver chiral alkynylated amines. © 2017 Taylor & Francis.EnglishAll Open Access; Bronze Open Access3,3,3 triethoxypropynealkene derivativealkyne derivativeprop 2 ynone derivativepropiophenoneunclassified drugArticleasymmetric synthesisbrominationcarbon nuclear magnetic resonancecatalystdecompositionelimination reactionhydrolysisnucleophilicityproton nuclear magnetic resonancepurificationstoichiometrysubstitution reactionsynthesisthin layer chromatographyArticle10.1080/00397911.2017.1376334