Improved reagent for electrophilic amination of stabilized carbanions

Org Lett. 2003 Oct 30;5(22):4187-90. doi: 10.1021/ol035629w.

Abstract

[reaction: see text]. Enolate amination using O-di(p-methoxyphenyl)phosphinylhydroxylamine 2 is reported. Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78 degrees C.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetonitriles / chemistry
  • Amination*
  • Anions / chemistry*
  • Catalysis
  • Hydroxylamines / chemistry
  • Malonates / chemistry
  • Molecular Structure
  • Organic Chemicals / chemistry*
  • Organophosphorus Compounds / chemistry
  • Phenylacetates / chemistry
  • Phosphinic Acids / chemistry

Substances

  • Acetonitriles
  • Anions
  • Hydroxylamines
  • Malonates
  • Organic Chemicals
  • Organophosphorus Compounds
  • Phenylacetates
  • Phosphinic Acids
  • benzyl cyanide