Stereoselective solid-phase synthesis of 3,4-substituted azetidinones as key intermediates for mono- and multicyclic β-lactam antibiotics and enzyme inhibitors

DELPICCOLO, C.M.L.; MATA, E.G

TETRAHEDRON-ASYMMETRY

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2002 vol. 13 p. 905 - 910

0957-4166

The polymer-supported Staudinger reaction proceeded smoothly under mild conditions to give the corresponding beta-lactams in good to high overall yields with excellent cis-selectivity. Upon applying this reaction system, an efficient asymmetric synthesis of beta-lactams was accomplished, when chiral acid chlorides or chiral aldehydes were used. These optically active beta-lactams would be useful precursors for the generation of combinatorial libraries of potential antibiotics and enzyme inhibitors