Iron(II)-catalyzed intermolecular amino-oxygenation of olefins through the N-O bond cleavage of functionalized hydroxylamines

J Am Chem Soc. 2014 Sep 24;136(38):13186-9. doi: 10.1021/ja508057u. Epub 2014 Sep 16.

Abstract

An iron-catalyzed diastereoselective intermolecular olefin amino-oxygenation reaction is reported, which proceeds via an iron-nitrenoid generated by the N-O bond cleavage of a functionalized hydroxylamine. In this reaction, a bench-stable hydroxylamine derivative is used as the amination reagent and oxidant. This method tolerates a range of synthetically valuable substrates that have been all incompatible with existing amino-oxygenation methods. It can also provide amino alcohol derivatives with regio- and stereochemical arrays complementary to known amino-oxygenation methods.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amination
  • Catalysis
  • Hydroxylamines / chemistry*
  • Iron / chemistry*
  • Oxidants / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Hydroxylamines
  • Oxidants
  • Iron