Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines. A practical synthesis of alpha-chiral amines.
The enantioselective addition of dialkylzinc reagents to N-diphenylphosphinoylimines derived from aryl-, furyl-, and cyclopropylaldehydes is efficiently catalyzed by a copper(II) triflate/(R,R)-MeDUPHOS complex. The yields are high (51-98%), and the enantiomeric excesses vary from 85 to 96%. This route provides a practical route to alpha-chiral amines.
Boezio
Alessandro A
AA
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Charette
André B
AB
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D017976:Phosphorus Acids / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D009942:Organometallic Compounds; D017976:Phosphorus Acids; C454811:diethylzinc