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%).
Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner, 50, E-46100-Burjassot, Spain.
Gonzalo
G
Blay
Isabel
I
Fernandez
Alícia
A
Marco-Aleixandre
José R
JR
Pedro
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