Alkene syn- and anti-oxyamination with malonoyl peroxides

Research output: Contribution to journalArticle

9 Downloads (Pure)

Abstract

Malonoyl peroxide [6] is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of [6] and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.
Original languageEnglish
Pages (from-to)1659-1664
Number of pages6
JournalOrganic Letters
Volume22
Issue number4
Early online date30 Jan 2020
DOIs
Publication statusPublished - 21 Feb 2020

Keywords

  • organic chemistry
  • Malonoyl peroxide
  • alkenes
  • alkene oxyamination

Fingerprint Dive into the research topics of 'Alkene syn- and anti-oxyamination with malonoyl peroxides'. Together they form a unique fingerprint.

Cite this