Monocyclic β-lactams were synthesized by a 1,3-cycloaddition/ thermal rearrangement process in the presence of a protic acid, starting from methylenecyclopropane derivatives and acyclic nitrones. Five-membered cyclic nitrones failed to give carbapenam structures under the same conditions, affording exclusively the corresponding N-trifluoroacetyl β- amino acid derivatives in the presence of trifluoroacetic acid.
Novel Prospects of the Acidic Thermal Rearrangement of Spirocyclopropane Isoxazolidines to β -Lactams / F. M. Cordero; M. Salvati; F. Pisaneschi; A. Brandi. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - 2004:(2004), pp. 2205-2213.
Novel Prospects of the Acidic Thermal Rearrangement of Spirocyclopropane Isoxazolidines to β -Lactams
CORDERO, FRANCA MARIA;SALVATI, MARIA;BRANDI, ALBERTO;
2004
Abstract
Monocyclic β-lactams were synthesized by a 1,3-cycloaddition/ thermal rearrangement process in the presence of a protic acid, starting from methylenecyclopropane derivatives and acyclic nitrones. Five-membered cyclic nitrones failed to give carbapenam structures under the same conditions, affording exclusively the corresponding N-trifluoroacetyl β- amino acid derivatives in the presence of trifluoroacetic acid.
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