Selective α-amination and α-acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates.
Selective α-amination and α-acylation of esters and amides have been developed, employing O-acylhydroxylamines as a dually reactive aminating and acylating reagent. Treatment of zinc enolates with O-acylhydroxylamines provides solely 1,3-dicarbonyl compounds under mild conditions. Introduction of a copper catalyst into the system shifts the reactivity entirely, yielding α-amination products exclusively.
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA. qiu.wang@duke.edu.
Stacey L
SL
McDonald
Qiu
Q
Wang
D000215:Acylation; D000577:Amides / Q000737:chemistry; D000586:Amination; D003300:Copper / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D006898:Hydroxylamines / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
D000577:Amides; D004952:Esters; D006898:Hydroxylamines; D017967:Zinc Compounds; D003300:Copper