Asymmetric, catalytic synthesis of alpha-chiral amines using a novel bis(phosphine) monoxide chiral ligand.
We have shown that Me-DuPHOS monoxide (BozPHOS) is a very effective ligand in the copper-catalyzed addition of dialkylzinc to N-phosphinoylimines providing access to alpha-chiral amines. The new ligand is particularly effective for the addition of the lesser reactive dimethylzinc. The major advantages of this process are high yields, broad substrate scope, and high enantioselectivities with low catalyst loading (3 mol %).
Boezio
Alessandro A
AA
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal (Québec), Canada H3C 3J7.
Pytkowicz
Julien
J
Côté
Alexandre
A
Charette
André B
AB
D000588:Amines / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000588:Amines; D009942:Organometallic Compounds; D010720:Phosphines; D003300:Copper; D015032:Zinc