Cobalt carbonyl-catalyzed carbonylative ring expansion of optically-pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans beta-lactam (8) afforded a key precursor of the carbapenem antibiotic (+)-PS-5. Aziridine (5) was obtained in both enantiomerically-pure forms by Amano PS lipase-catalyzed esterification in n.hexane using vinyl acetate as acyl donor. The stereochemical pathway of the carbonylation reaction was proved by configurational assignments through chemical correlation.
A novel approach to a precursor of the carbapenem antibiotic PS-5 via aziridine stereospecific carbonylation / Davoli, Paolo; Prati, Fabio. - In: HETEROCYCLES. - ISSN 0385-5414. - STAMPA. - 53:11(2000), pp. 2379-2389. [10.3987/COM-00-8974]
A novel approach to a precursor of the carbapenem antibiotic PS-5 via aziridine stereospecific carbonylation
DAVOLI, Paolo;PRATI, Fabio
2000
Abstract
Cobalt carbonyl-catalyzed carbonylative ring expansion of optically-pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans beta-lactam (8) afforded a key precursor of the carbapenem antibiotic (+)-PS-5. Aziridine (5) was obtained in both enantiomerically-pure forms by Amano PS lipase-catalyzed esterification in n.hexane using vinyl acetate as acyl donor. The stereochemical pathway of the carbonylation reaction was proved by configurational assignments through chemical correlation.
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