ENANTIOSELECTIVE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE CATALYZED BY TI(IV) AND GLUCOSE DERIVATIVES

JOSÉ PARADA, JORGE MENDOZA, FRANCY CISTERNAS, ANGEL EGUILUZ
2010 Journal of the Chilean Chemical Society (Print)  
D-Glucose derivatives 1,2:5,6-di-O-isopropyline-a-D-glucofuranose (1) and 1,2-O-isopropyline-a-D-glucofuranose (2) with Ti(IV) are chiral catalysts in the addition of diethylzinc to benzaldehyde. The Ti(IV)-carbohydrate catalytic system is optimal with excess Ti(IV) and substoichiometric carbohydrate and 2 is the more active chiral catalyst probably because this derivative acts as a bidentate ligand in the proposed reaction. The arrangement of OH groups is crucial in determining the
more » ... ing the configuration of the alcohol product.
doi:10.4067/s0717-97072010000400003 fatcat:vciji3dhtndfvn63g3g7k75zdy