Catalytic, Enantioselective Syn-Oxyamination of Alkenes

Emily M. Mumford, Brett N. Hemric, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review

Abstract

The chemo-, regio-, diastereo-, and enantioselective 1,2-oxyamination of alkenes using selenium(II/IV) catalysis with a chiral diselenide catalyst is reported. This method uses N-tosylamides to generate oxazoline products that are useful both as protected 1,2-amino alcohol motifs and as chiral ligands. The reaction proceeds in good yields with excellent enantio- and diastereoselectivity for a variety of alkenes and pendant functional groups such as sulfonamides, alkyl halides, and glycol-protected ketones. Furthermore, the rapid generation of oxazoline products is demonstrated in the expeditious assembly of chiral PHOX ligands as well as diversely protected amino alcohols.

Original languageEnglish (US)
Pages (from-to)13408-13417
Number of pages10
JournalJournal of the American Chemical Society
Volume143
Issue number33
DOIs
StatePublished - Aug 25 2021

ASJC Scopus subject areas

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

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