The reactivity of in situ generated organozinc reagents of 3-alkenyl-3-bromoazetidin-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 the preparation of the corresponding keto derivatives. The products of these reactions could be of interest on account of their structural similarity with the already known cholesterol adsorption inhibitors
Zinc metal-promoted nucleophilic addition of azetidin-2-ones to aldehydes and nitriles
PICCINELLI, FABIO;
2005-01-01
Abstract
The reactivity of in situ generated organozinc reagents of 3-alkenyl-3-bromoazetidin-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 the preparation of the corresponding keto derivatives. The products of these reactions could be of interest on account of their structural similarity with the already known cholesterol adsorption inhibitors
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