Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products

Title: Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products

Volume: 11 Issue: 14

Author(s): C. Palomo, J. M. Aizpurua, I. Ganboa and M. Oiarbide

Affiliation:

Keywords: lactams, amino acids, peptides, imines, staudinger reaction, asymmetric synthesis

Abstract: In the last two decades, the better understanding of the mechanistic aspects of the β-lactams biological activity and their inhibition, and the chemical exploitation of β-lactams as synthetic intermediates in organic chemistry, have experienced a continuous and somewhat complementary advance. A prerequisite for such a development has been the accessibility of enantiopure β-lactams. The latter are now routinely prepared most often through the ketene-imine cycloaddition reaction, also termed the Staudinger reaction. This review accounts for the recent progress made in the asymmetric synthesis of β-lactams (with special emphasis in the Staudinger reaction approach), as well as in their use as synthetic intermediates en route to natural products, including α- and β-amino acids and peptides derived therefrom.

Cite this article as:

Palomo C., Aizpurua M. J., Ganboa I. and Oiarbide M., Asymmetric Synthesis of β-Lactams Through the Staudinger Reaction and Their Use as Building Blocks of Natural and Nonnatural Products, Current Medicinal Chemistry 2004; 11 (14) . https://dx.doi.org/10.2174/0929867043364900