Research Information System
Synthetic Communications, vol.47, no.24, pp.2342-2351, 2017 (SCI-Expanded)
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.