N -Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/brønsted acid Co-catalyzed allylic C-H oxidation

Thomas J. Osberger, M. Christina White

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)11176-11181
Number of pages6
JournalJournal of the American Chemical Society
Volume136
Issue number31
DOIs
StatePublished - Aug 6 2014

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry

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