FeCl3·6H2O, a catalyst for the diastereoselective synthesis of cis-isoxazolidines from N-protected δ-hydroxylamino allylic acetates

J Org Chem. 2013 Oct 18;78(20):10273-87. doi: 10.1021/jo401627p. Epub 2013 Oct 4.

Abstract

An ecofriendly and diastereoselective synthesis of cis-3,5-disubstituted isoxazolidines through the FeCl3·6H2O-catalyzed cyclization of δ-hydroxylamino allylic acetates is described. The synthetic potential of these products is highlighted by the preparation of several functionalized 1,3-amino alcohol precursors.

MeSH terms

  • Acetates / chemistry*
  • Allyl Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Hydroxylamines / chemistry*
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acetates
  • Allyl Compounds
  • Hydroxylamines
  • Isoxazoles
  • allyl acetate