Ontology highlight
ABSTRACT:
SUBMITTER: Krenske EH
PROVIDER: S-EPMC3642281 | biostudies-literature | 2013 Apr
REPOSITORIES: biostudies-literature
Journal of the American Chemical Society 20130401 14
Cycloadditions involving oxyallyl intermediates typically require an electron-rich diene or alkene, but we have discovered the first examples of the cycloaddition of heteroatom-stabilized oxyallyls onto carbonyl groups. An oxazolidinone-substituted oxyallyl undergoes chemoselective (3 + 2) cycloaddition onto the carbonyl group of a tethered dienone in preference to formation of the expected (4 + 3) cycloadduct. Density functional theory calculations indicated that the (3 + 2) cycloaddition takes ...[more]