MeOTf-mediated alkynylation of selenoamides leading to beta-methylselenenyl alpha,beta-unsaturated ketones and their characterization.

ABSTRACT

[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.