syn-1,2-amino alcohols via diastereoselective allylic C-H amination

Kenneth J. Fraunhoffer, M. Christina White

Research output: Contribution to journalArticle

Abstract

A novel Pd/sulfoxide catalyzed diastereoselective allylic C-H amination reaction of chiral homoallylic N-tosyl carbamates is reported. Densely oxygenated ∞-olefin substrates with multiple stereogenic centers undergo allylic C-H amination in excellent yields and with diastereoselectivities that are controlled by the stereocenter that bears the N-tosyl carbamate. Streamlined routes to stereochemically defined anti-oxazolidinones that can be further elaborated to medicinally and biologically relevant 1,2-amino alcohols are also demonstrated. Evidence is provided that this reaction proceeds via a Pd/sulfoxide-mediated allylic C-H cleavage to form a π-allylPd intermediate followed by Pd(II) counterion-assisted deprotonation of the nitrogen nucleophile to effect functionalization.

Original languageEnglish (US)
Pages (from-to)7274-7276
Number of pages3
JournalJournal of the American Chemical Society
Volume129
Issue number23
DOIs
StatePublished - Jun 13 2007

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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