Synthetic Study of cis-3-Amino-4-(1-hydroxyalkyl)azetidin-2-ones Using L-Aspartic Acid as a Chiral Synthon

Abstract

The stereoselective synthesis of cis-3-amino-4-(1-hydroxyalkyl)azetidin-2-ones from L-aspartic acid is described. The thermodynamically less stable isomers with 3, 4-cis stereochemistry, key intermediates for the synthesis of various substitutes monobactams, were obtained by hydrogenation of the 3-oxyimino-azetidin-2-ones prepared from azetidin-2-ones and isoamyl nitrite. Furthermore, some simple analogues of monobactams were synthesized.