Collect. Czech. Chem. Commun. 1991, 56, 2352-2361

Preparation of 7-spiroepoxy and 7,7-disubstituted cephalosporanate 1,1-dioxide from 7-diazocephalosporanate 1,1-dioxide: Reactions of 7-diazocephalosporanate 1,1-dioxide with aldehydes

David Czajkowski, Oludotun A. Phillips, Narender A. V. Reddy, Paul Spevak, Bruce Lix, Ronald G. Micetich and Samarendra N. Maiti*

SynPhar Laboratories Inc., No. 24, 4290-91A St., Taiho Alberta Centre, Edmonton, Alberta, Canada T6E 5V2


The reactions of tert-butyl-3-acetoxymethyl-3-cephem-7-diazocephalosporanate 1,1-dioxide (I) with acetaldehyde, benzaldehyde, 2-thiophene caboxaldehyde, 3-thiophene carboxaldehyde, 2-furan carboxaldehyde, 3-furan carboxaldehyde and isobutyraldehyde have been studied. Use of boron trifluoride etherate as a catalyst for these reactions was found to accelerate the reactions markedly and to favour the formation of aldehydes rather than the ketones at C-7 position as the carbonyl product. The products obtained from these reactions and the ratios of carbonyl products to epoxides suggest that the R groups of the carbonyl component have profound influence on the reactions.