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.
Lipase-Catalyzed Resolution and Desymmetrization of 2-Hydroxymethylaziridines / Davoli, Paolo; Caselli, Emilia; Bucciarelli, Maria; Forni, Arrigo; Torre, Giovanni; Prati, Fabio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1. - ISSN 1472-7781. - STAMPA. - 17(2002), pp. 1948-1953.
Data di pubblicazione: | 2002 |
Titolo: | Lipase-Catalyzed Resolution and Desymmetrization of 2-Hydroxymethylaziridines |
Autore/i: | Davoli, Paolo; Caselli, Emilia; Bucciarelli, Maria; Forni, Arrigo; Torre, Giovanni; Prati, Fabio |
Autore/i UNIMORE: | |
Rivista: | |
Volume: | 17 |
Pagina iniziale: | 1948 |
Pagina finale: | 1953 |
Codice identificativo ISI: | WOS:000177605000004 |
Codice identificativo Scopus: | 2-s2.0-0036025612 |
Citazione: | Lipase-Catalyzed Resolution and Desymmetrization of 2-Hydroxymethylaziridines / Davoli, Paolo; Caselli, Emilia; Bucciarelli, Maria; Forni, Arrigo; Torre, Giovanni; Prati, Fabio. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. 1. - ISSN 1472-7781. - STAMPA. - 17(2002), pp. 1948-1953. |
Tipologia | Articolo su rivista |
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