Journal of the Chilean Chemical Society
versión On-line ISSN 0717-9707
PARADA, JOSÉ; MENDOZA, JORGE; CISTERNAS, FRANCY y EGUILUZ, ANGEL. ENANTIOSELECTIVE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE CATALYZED BY TI(IV) AND GLUCOSE DERIVATIVES. J. Chil. Chem. Soc. [online]. 2010, vol.55, n.4, pp. 428-430. ISSN 0717-9707. http://dx.doi.org/10.4067/S0717-97072010000400003.
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 configuration of the alcohol product.
Palabras clave : diethylzinc; glucose derivatives; 1- phenyl-1-propanol; Ti (IV)-carbohydrate.