Authors: Aranda, M. T.; Perez-Faginas, Paula; Gonzalez-Muniz, Rosario

Source: Current Organic Synthesis, Volume 6, Number 3, August 2009 , pp. 325-341(17)

Publisher: Bentham Science Publishers

Abstract:

Because the renewed interest of β-lactams in organic and medicinal chemistry, research in this field continues in producing new appealing progresses. This review tries to call the attention on synthetic aspects related to the generation of the four-membered heterocyclic ring, published in the last few years, with special accent in stereoselective synthetic approaches. The compendium will cover methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as the first choice method, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition, and the Kinugasa reaction. Significant success was also obtained 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, the 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

Document Type: Research article

DOI: http://dx.doi.org/10.2174/157017909788921899

Publication date: 2009-08-01

More about this publication?

• Current Organic Synthesis publishes in-depth reviews on all areas of synthetic organic chemistry i.e. asymmetric synthesis, organometallic chemistry, novel synthetic approaches to complex organic molecules, carbohydrates, polymers, protein chemistry, DNA chemistry, supramolecular chemistry, molecular recognition and new synthetic methods in organic chemistry. The frontier reviews provide the current state of knowledge in these fields and are written by experts who are internationally known for their eminent research contributions. The journal is essential reading to all synthetic organic chemists. Current Organic Synthesis should prove to be of great interest to synthetic chemists in academia and industry who wish to keep abreast with recent developments in key fields of organic synthesis.

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