Practical synthesis of functionalized terminal alkynes, 3,3,3-triethoxypropyne and ketal protected prop-2-ynones
No Thumbnail Available
Date
2017
Authors
Journal Title
Journal ISSN
Volume Title
Publisher
Abstract
Practical 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.
Description
Keywords
3,3,3 triethoxypropyne , alkene derivative , alkyne derivative , prop 2 ynone derivative , propiophenone , unclassified drug , Article , asymmetric synthesis , bromination , carbon nuclear magnetic resonance , catalyst , decomposition , elimination reaction , hydrolysis , nucleophilicity , proton nuclear magnetic resonance , purification , stoichiometry , substitution reaction , synthesis , thin layer chromatography