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

Full Text: HTML

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 ...

Related Articles:

β-Lactam formation by ultrasound-promoted reformatsky type reaction

[Bose, Ajay K.; Gupta, Kavita; Manhas, M. S. Journal of the Chemical Society, Chemical Communications, 1984 , # 2 p. 86 - 87]

The synthesis of β-lactams via a one-pot Reformatsky reaction of imines promoted by Zn/Cp 2 TiCl 2 (cat.)

[Chen, Lei; Zhao, Gang; Ding, Yu Tetrahedron Letters, 2003 , vol. 44, # 12 p. 2611 - 2614]

N, N-Dimethylphosphoramidic dichloride: a convenient reagent for the preparation of β-lactams from acetic acids and imines

[Cossio, Fernando P.; Ganboa, Inaki; Garcia, Jesus M.; Lecea, Begona; Palomo, C. Tetrahedron Letters, 1987 , vol. 28, # 17 p. 1945 - 1948]

More Articles...