Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.

ABSTRACT: Vinyl oxazolidinones react with DDQ to form alpha,beta-unsaturated acyliminium ions in a new method for forming electrophiles under oxidative conditions. Appended nucleophiles undergo 1,4-addition reactions with these intermediates to form cyclic vinyl oxazolidinones with good levels of diastereocontrol, highlighting a new approach to utilizing oxidative carbon-hydrogen bond functionalization to increase molecular complexity.

SUBMITTER: Liu L 

PROVIDER: S-EPMC2722373 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature