Palladium-mediated regiodivergent kinetic resolution.
[reaction: see text]. The allylic substitution of racemic 5-vinyloxazolidinones with phthalimide and a chiral palladium catalyst afforded optically enriched regioisomeric products. Optimal divergence was found by employing chiral DIOP ligands in toluene. These results demonstrate the influence of chiral ligand/chiral substrate matching on the regioselectivity in a novel resolution strategy.
Cook
G R
GR
Department of Chemistry, North Dakota State University, Fargo, North Dakota 58105-5516, USA. gregory.cook@ndsu.nodak.edu
Sankaranarayanan
S
S
D007202:Indicators and Reagents; D007700:Kinetics; D023303:Oxazolidinones / Q000138:chemical synthesis*; D010165:Palladium; D010797:Phthalimides / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D023303:Oxazolidinones; D010797:Phthalimides; D014753:Vinyl Compounds; D010165:Palladium