Hydroxyamination of olefins using Br-N-(CO2Me)2

J Org Chem. 2015 Feb 6;80(3):1440-5. doi: 10.1021/jo502369d. Epub 2015 Jan 22.

Abstract

The hydroxyamination reagent Br-N-(CO2Me)2 underwent Markovnikov addition to various olefins in the presence of catalytic BF3·OEt2 and provides efficient access to aminoalcohols. The reaction provided the trans-1-bromo, 2-N-bis-carbamate adduct stereoisomer in all cases. The resulting adduct underwent cyclization to give an oxazolidinone, which could be readily hydrolyzed to an oxazolidin-2-one or an amino alcohol.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemistry*
  • Amination
  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry*
  • Carbamates / chemical synthesis*
  • Carbamates / chemistry*
  • Catalysis
  • Cyclization
  • Indicators and Reagents / chemistry
  • Magnetic Resonance Spectroscopy
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Amino Alcohols
  • Carbamates
  • Indicators and Reagents
  • Oxazolidinones
  • trans-1-bromo-2-N-bis-carbamate