B. Trofimov, T. E. Glotova, M. Dvorko
Sep 18, 2010
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract Triphenylphosphine catalyzes the regio- and stereospecific addition of ketoximes to acylacetylenes, whereas classical conditions using acetylene (KOH/DMSO, 70 °C) are unsuitable for this purpose. The reaction proceeds under mild conditions (CH 2 Cl 2 , rt, 7 h) to afford ( E )-( O )-2-(acyl)vinylketoximes (92–98% stereoselectivity) in a yield of up to 85%. The ( E )-adducts obtained are energetically less favorable than the corresponding ( Z )-isomers and are gradually enriched with ( Z )-isomers, thus indicating the kinetic control of ( E )-stereoselectivity of the reaction.