Advances in Organic Synthesis

Volume: 6

Indexed in: Scopus, EBSCO, Ulrich's Periodicals Directory

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. It presents comprehensive articles written by eminent authorities ...
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An Update on the Synthesis of β-Lactams

Pp. 296-354 (59)

M. Teresa Aranda, Paula Pérez-Faginas and Rosario González-Muñiz

Abstract

As a consequence of the renewed interest of β–lactams in organic and medicinal chemistry, research in this field is constantly providing new appealing advances. This chapter focuses on synthetic aspects related to the generation of this four-membered heterocyclic ring, published since 2000, with special emphasis on stereoselective synthetic approaches. The compendium deals with methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as first choice, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition and the Kinugasa reaction. Significant success has also been accomplished in the synthesis of innovative 2-azetidinones through the formation of a single bond. In this respect, the C3-C4 bond formation, through intramolecular cyclization of linear epoxy or halo derivatives and the carbenoid C-H insertion are among the most effectively exploited procedures. In addition, adaptation of most procedures to solid-phase methodologies has facilitated the generation of molecular diversity based on the β–lactam skeleton.

Keywords:

β–lactams, 2-azetidinones, stereoselective synthesis, chiral auxiliaries, chiral catalysts, memory of chirality.

Affiliation:

Instituto de Química Médica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.