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

Citation
T. Murai et al., MeOTf-mediated alkynylation of selenoamides leading to beta-methylselenenyl alpha,beta-unsaturated ketones and their characterization, ORG LETT, 3(13), 2001, pp. 1993-1995
Citations number
26
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
1523-7060 → ACNP
Volume
3
Issue
13
Year of publication
2001
Pages
1993 - 1995
Database
ISI
SICI code
1523-7060(20010628)3:13<1993:MAOSLT>2.0.ZU;2-I
Abstract
beta -Methylselenenyl alpha,beta -unsaturated ketones were effectively synt hesized by treating selenoamides with methyl triflate, followed by reaction with lithium acetylides, The reaction proceeded with high stereoselectivit y to give exclusively Z-isomers, Se-77 NMR studies and X-ray molecular stru cture analysis of beta -methylselenenyl alpha,beta -unsaturated ketones sug gested that the products show 1,5-nonbonding interaction between the seleni um atom and carbonyl oxygen atom.