Organoselenium-Catalyzed Enantioselective Synthesis of 2-Oxazolidinones from Alkenes
Carter C. Cunningham, Jesse L. Panger, Michela Lupi, Scott E. Denmark
Abstract
An operationally simple method for generating enantioenriched 2-oxazolidinones from N -Boc amines and mono- or trans- disubstituted alkenes via chiral organoselenium catalysis is described. Critical to the success of the transformation was the inclusion of triisopropylsilyl chloride (TIPSCl), likely because it sequestered fluoride generated by the oxidant ( N -fluorocollidinium tetrafluoroborate) throughout the reaction and suppressed side reactivity. The scope of both the amine and alkene substrates was explored, generating a variety of 2-oxazolidinones in modest to high yields with high enantioselectivities.
Topics & Concepts
ChemistryEnantioselective synthesisAlkeneCatalysisTetrafluoroborateReactivity (psychology)Amine gas treatingOrganic chemistryCombinatorial chemistryChlorideIonic liquidAlternative medicinePathologyMedicineChemical Synthesis and ReactionsSulfur-Based Synthesis TechniquesAsymmetric Synthesis and Catalysis