Exploring the Solid-Phase Synthesis of 3,4-Disubstituted ß-Lactams: Scope and Limitations

CARINA DELPICCOLO,; MÉNDEZ, LUCIANA; FRAGA, MARIA AMELIA; ERNESTO G. MATA

J. Comb. Chem.

ACS

Lugar: Washington (USA); Año: 2005 vol. 7 p. 331 - 344

1520-4766

This work describes a comprehensive study on the solid-phase synthesis of 3,4-disubstituted b-lactams. In situ generated ketenes react with immobilized aldimines under mild conditions to generate libraries of b-lactams in good to very good overall isolated yields. Different commercially available solid supports were studied, being the cost-effective Wang resin the most effective. The utility of the protocol was also demonstrated by the highly efficient asymmetric versions when homochiral ketenes or homochiral aldimines were used. A practical technique for the preparation of manual solid-phase parallel libraries of biologically interesting b-lactam compounds, using Mukaiyama’s salt as dehydrating agent, is also presented. Reactions were easily monitored by FT-IR and gel-phase 13C NMR using conventional equipment