title: N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.
abstract: A Pd(II)/bis-sulfoxide/Brønsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
authors.affiliation: Roger Adams Laboratory, University of Illinois Urbana-Champaign , Champaign, Illinois 61801, United States.
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Osberger
authors.forename: M Christina
authors.initials: MC
authors.lastname: White
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D023303:Oxazolidinones / Q000737:chemistry*; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013454:Sulfoxides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D000588:Amines; D023303:Oxazolidinones; D013454:Sulfoxides; D010165:Palladium; D002244:Carbon; D010100:Oxygen