A highly enantioselective synthesis of beta-lactams "via" a [2+2] cycloaddition reaction of homochiral tricarbonyl[N-(2-methoxybenzylidene)aniline]chromium with ketene is reported. Moreover the reaction of (+)-(1S)-tricarbonyl[N-(2-methoxybenzylidene)aniline]chromium with acethoxy ketene gives the corresponding 4-styryl-beta-lactam in good yield but with moderate stereoselection.
Baldoli, C., DEL BUTTERO, P., Licandro, E., Maiorana, S., Papagni, A. (1994). TRICARBONYL(ETA(6) ARENE)CHROMIUM(0) COMPLEXES AS CHIRAL AUXILIARIES - HOMOCHIRAL-BETA-LACTAMS SYNTHESIS VIA [2+2] CYCLOADDITION REACTION. TETRAHEDRON-ASYMMETRY, 5(5), 809-812 [10.1016/S0957-4166(00)86233-3].
TRICARBONYL(ETA(6) ARENE)CHROMIUM(0) COMPLEXES AS CHIRAL AUXILIARIES - HOMOCHIRAL-BETA-LACTAMS SYNTHESIS VIA [2+2] CYCLOADDITION REACTION
PAPAGNI, ANTONIO
1994
Abstract
A highly enantioselective synthesis of beta-lactams "via" a [2+2] cycloaddition reaction of homochiral tricarbonyl[N-(2-methoxybenzylidene)aniline]chromium with ketene is reported. Moreover the reaction of (+)-(1S)-tricarbonyl[N-(2-methoxybenzylidene)aniline]chromium with acethoxy ketene gives the corresponding 4-styryl-beta-lactam in good yield but with moderate stereoselection.
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