Cyclization reactions through DDQ-mediated vinyl oxazolidinone oxidation.
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.
Liu
Lei
L
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Floreancig
Paul E
PE
D016227:Benzoquinones / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D016227:Benzoquinones; D023303:Oxazolidinones; D014753:Vinyl Compounds; C000928:dichlorodicyanobenzoquinone