Catalytic asymmetric addition of dimethylzinc to alpha-ketoesters, using mandelamides as ligands.
[reaction: see text] A strategy based on the control of the electron-donating capabilities of the coordinating groups of the ligand has been applied in the catalytic asymmetric addition of organometallic reagents to ketoesters. Mandelamides having deprotonated alcohol and carboxyamido groups catalyzed the addition of dimethylzinc to alpha-ketoesters with good yields and ee (up to 90%).
Blay
Gonzalo
G
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner, 50, E-46100-Burjassot, Spain.
Fernandez
Isabel
I
Marco-Aleixandre
Alícia
A
Pedro
José R
JR
D002384:Catalysis; D004952:Esters; D008024:Ligands; D008333:Mandelic Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*
D004952:Esters; D008024:Ligands; D008333:Mandelic Acids; C010413:mandelamide; D015032:Zinc