The reactivity of in situ generated organozinc reagents of 3-bromo-3-alkenyl-azetidin-2-ones with aromatic and aliphatic aldehydes to give the corresponding alcohol derivatives has been studied. The effect of solvent and Lewis acids has been explored in order to improve the reaction yields. The application of this methodology to nitriles and acyl chlorides allowed to prepare keto-derivatives. The products of these reactions could be of interest for their structural similarity with already known cholesterol adsorption inhibitors
F. Benfatti, G. Cardillo, S. Fabbroni, L. Gentilucci, R. Perciaccante, F. Piccinelli, et al. (2005). Zinc Metal-Promoted Nucleophilic Addition of Azetidin-2-ones to Aldehydes and Nitriles. SYNTHESIS, 1, 61-70 [10.1055/s-2004-834897].
Zinc Metal-Promoted Nucleophilic Addition of Azetidin-2-ones to Aldehydes and Nitriles
BENFATTI, FIDES;CARDILLO, GIULIANA;FABBRONI, SERENA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;PICCINELLI, FABIO;TOLOMELLI, ALESSANDRA
2005
Abstract
The reactivity of in situ generated organozinc reagents of 3-bromo-3-alkenyl-azetidin-2-ones with aromatic and aliphatic aldehydes to give the corresponding alcohol derivatives has been studied. The effect of solvent and Lewis acids has been explored in order to improve the reaction yields. The application of this methodology to nitriles and acyl chlorides allowed to prepare keto-derivatives. The products of these reactions could be of interest for their structural similarity with already known cholesterol adsorption inhibitorsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
