Application of nitrones in the stereoselective synthesis of important β-lactam compounds

Institute of Organic Chemistry PAS, Warsaw, Poland
DOI
10.7287/peerj.preprints.1917v1
Subject Areas
Drugs and Devices, Synthetic Biology
Keywords
nitrones, Kinugasa reaction, β-lactams
Copyright
© 2016 Chmielewski
Licence
This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, reproduction and adaptation in any medium and for any purpose provided that it is properly attributed. For attribution, the original author(s), title, publication source (PeerJ Preprints) and either DOI or URL of the article must be cited.
Cite this article
Chmielewski M. 2016. Application of nitrones in the stereoselective synthesis of important β-lactam compounds. PeerJ Preprints 4:e1917v1

Abstract

The copper(I)-mediated reaction of nitrones with terminal acetylenes, known as the Kinugasa reaction, represents an attractive method of direct formation of the β-lactam ring. The reaction can be performed in many ways. Diastereoselective versions, including cyclic chiral nitrones or chiral acetylenes and open-chain nitrones, are the most attractive. An alternative method yielding β-lactams with high stereoselectivity, in which nitrones are used, is their 1,3-dipolar cycloaddition to unsaturated lactones. After N- O bond cleavage, cycloadducts can be easily transformed into β-lactams via an intramolecular acylation of the nitrogen atom. Both methodologies are demonstrated in the synthesis of carbapenems (Thienamycin and 4AA azetidinone), monobactams (Carumonam) and Ezetimibe, a powerful cholesterol absorption inhibitor.

Author Comment

This is an Abstract submitted to the X MKNOL Conference.