Synthesis 2005(1): 61-70  
DOI: 10.1055/s-2004-834897
PAPER
© Georg Thieme Verlag Stuttgart · New York

Zinc Metal-Promoted Nucleophilic Addition of Azetidin-2-ones to Aldehydes and Nitriles

Fides Benfatti, Giuliana Cardillo*, Serena Fabbroni, Luca Gentilucci, Rossana Perciaccante, Fabio Piccinelli, Alessandra Tolomelli
Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: giuliana.cardillo@unibo.it;
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Publikationsverlauf

Received 27 July 2004
Publikationsdatum:
02. November 2004 (online)

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.

9

The reactions were performed on racemic mixtures. For the sake of simplicity only one enantiomer has been reported in the schemes.

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Detailed X-ray data for 3a and 3b are reported in the experimental section. CCDC number for 3a is 245012, CCDC number for 3b is 245013.