Enantioselective addition of diethyl zinc to benzaldehyde catalyzed by ti(iv) and glucose derivatives

• JOSÉ PARADA ^[1] ; JORGE MENDOZA ^[1] ; FRANCY CISTERNAS ^[1] ; ANGEL EGUILUZ ^[1]
  1. [1] Universidad de Chile

     Universidad de Chile

     Santiago, Chile

     
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 55, Nº. 4, 2010, págs. 428-430
• Idioma: inglés
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• Resumen

  • 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.