MeOTf-mediated alkynylation of selenoamides leading to beta-methylselenenyl alpha,beta-unsaturated ketones and their characterization.
[reaction: see text] beta-Methylselenenyl alpha,beta-unsaturated ketones were effectively synthesized by treating selenoamides with methyl triflate, followed by reaction with lithium acetylides. The reaction proceeded with high stereoselectivity to give exclusively Z-isomers. (77)Se NMR studies and X-ray molecular structure analysis of beta-methylselenenyl alpha,beta-unsaturated ketones suggested that the products show 1,5-nonbonding interaction between the selenium atom and carbonyl oxygen atom.
Murai
T
T
Department of Chemistry, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan. mtoshi@cc.gifu-u.ac.jp
Mutoh
Y
Y
Kato
S
S