Enantioselective Enolate Protonation in Sulfa-Michael Addition to α-Substituted N-Acryloyloxazolidin-2-ones with Bifunctional Organocatalyst

Organocatalytic conjugate addition of thiols to alpha-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules.