An efficient chemoselective general procedure for the synthesis of γ-substituted β,γ-unsaturated α-ketomethylthioesters from α,β-unsaturated ketones has been achieved through an unprecedented PPh3·HBr-DMSO mediated oxidative bromination and Kornblum oxidation sequence. The newly developed reagent system serves admirably for the synthesis of α-bromoenals from enals. Furthermore, AuCl 3-catalyzed efficient access to 3(2H)-furanones from the above intermediates under extremely mild conditions are described.
- oxidative bromination
- triphenylphosphine hydrobromide
ASJC Scopus subject areas
- Organic Chemistry