The effect of ring substituents on the cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to β-lactams has been investigated. A variety of aziridines with different substituents and stereochemistry has been synthesized and subjected to carbonylation. The ring expansion to β-lactam takes place in the absence of an electron-withdrawing substituent and higher yields are always obtained for cis-aziridines. Moreover, the regioselectivity of the reaction is affected by the nature of substituents at ring carbon atoms
On the Efffect of Ring Substituent in the Carbonylation of Aziridines / Davoli, Paolo; Forni, Arrigo; Moretti, Irene; Torre, Giovanni; Prati, Fabio. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 57:9(2001), pp. 1801-1812. [10.1016/S0040-4020(00)01152-2]
On the Efffect of Ring Substituent in the Carbonylation of Aziridines
DAVOLI, Paolo;FORNI, Arrigo;MORETTI, Irene;TORRE, Giovanni;PRATI, Fabio
2001
Abstract
The effect of ring substituents on the cobalt carbonyl-catalyzed carbonylation of functionalized aziridines to β-lactams has been investigated. A variety of aziridines with different substituents and stereochemistry has been synthesized and subjected to carbonylation. The ring expansion to β-lactam takes place in the absence of an electron-withdrawing substituent and higher yields are always obtained for cis-aziridines. Moreover, the regioselectivity of the reaction is affected by the nature of substituents at ring carbon atoms
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