Novel N1-C4 beta-lactam bond breakage. Synthesis of enantiopure alpha-alkoxy-gamma-keto acid derivatives.
Addition reaction of 2-(trimethylsilyl)thiazole (TMST) to cis- or trans-4-formyl-beta-lactams gave enantiopure alpha-alkoxy-gamma-keto acid derivatives via a novel N1-C4 bond breakage of the beta-lactam nucleus. This is the first time that the cleavage of the N1-C4 bond on the beta-lactam nucleus has been shown to occur in 2-azetidinones lacking an aryl moiety at C4. [reaction--see text]
Alcaide
Benito
B
Departamento de Química Orgánica, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Redondo
María C
MC