Improved reagent for electrophilic amination of stabilized carbanions.
[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.
Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.
Jason A
JA
Smulik
Edwin
E
Vedejs
D000097:Acetonitriles / Q000737:chemistry; D000586:Amination; D000838:Anions / Q000737:chemistry*; D002384:Catalysis; D006898:Hydroxylamines / Q000737:chemistry; D008314:Malonates / Q000737:chemistry; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D010648:Phenylacetates / Q000737:chemistry; D010721:Phosphinic Acids / Q000737:chemistry
D000097:Acetonitriles; D000838:Anions; D006898:Hydroxylamines; D008314:Malonates; D009930:Organic Chemicals; D009943:Organophosphorus Compounds; D010648:Phenylacetates; D010721:Phosphinic Acids; C006725:benzyl cyanide