The Reformatskii type reaction of Gilman and Speeter in the preparation of valuable. beta.-lactams in carbapenem synthesis: scope and synthetic utility

…, A Arrieta, JM Odriozola, M Oiarbide…

Index: Palomo, Claudio; Cossio, Fernando P.; Arrieta, Ana; Odriozola, Jose M.; Oiarbide, Mikel; Ontoria, Jesus M. Journal of Organic Chemistry, 1989 , vol. 54, # 24 p. 5736 - 5745

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Citation Number: 39

Abstract

The preparation of appropriately substituted 3-alkyl p-lactams from the Reformatsky type reaction of Gilman and Speeter is described. Treatment of Schiff bases derived from a- methylcinnamaldehyde and amines with ethyl a-bromobutyrate or ethyl a-bromoisovalerate in the presence of zinc dust followed by an ozonolysis-Baeyer-Viger sequence of the resulting p-ladams afforded 3-alkyl-4-acetoxy@-lactams as synthetic intermediates for the ...