315696-02-7Relevant academic research and scientific papers
Lipase-catalyzed resolution and desymmetrization of 2-hydroxymethylaziridines
Davoli, Paolo,Caselli, Emilia,Bucciarelli, Maria,Forni, Arrigo,Torre, Giovanni,Prati, Fabio
, p. 1948 - 1953 (2007/10/03)
The Amano PS lipase-catalyzed acetylation of 2-hydroxymethylaziridines 1a-e has been investigated in order to evaluate the effect of ring substituents on the enantioselectivity of the reaction and to assess the stereochemical preference of the enzyme. N-Benzyl-3-substituted cis-aziridines displayed high enantioselectivity and higher E values were found when the bulkiness of the substituent in position 3 was increased. In contrast, the corresponding trans isomers showed only poor enantioselectivity, regardless of the steric hindrance of the substituent at C3. Removal of the N-benzyl group proved to be detrimental to the enantioselectivity. In addition, desymmetrization of meso dimethanolic cis-aziridine 1f was successfully accomplished, and the corresponding monoacetylated product 2f, which is related to a key intermediate used in the total synthesis of the mitomycin antibiotic FR-900482, was obtained in excellent yield and nearly enantiomerically pure form. Moreover, the absolute configuration of enantiomerically pure cis-aziridines was determined by chemical correlation and/or chiroptical techniques, thus showing the stereochemical preference of Amano PS lipase for the 2S enantiomer.
A novel approach to a precursor of the carbapenem antibiotic PS-5 via aziridine stereospecific carbonylation
Davoli, Paolo,Prati, Fabio
, p. 2379 - 2389 (2007/10/03)
Cobalt carbonyl-catalyzed carbonylative ring expansion of optically pure cis-1-benzyl-3-ethyl-2-hydroxymethylaziridine (5) to trans-β-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.
