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The allylic substitution of racemic 5-vinyloxazolidinones with phthalimide
and a chiral palladium catalyst afforded optically enriched regioisomeric p
roducts. Optimal divergence was found by employing chiral DIOP ligands in t
oluene. These results demonstrate the influence of chiral ligand/chiral sub
strate matching on the regloselectivity in a novel resolution strategy.