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Issue 1, 2017
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Recent advances in the chemistry of metallated azetidines

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Abstract

The almost unexplored four-membered heterocycles azetidines, represent a particularly interesting class of molecules, among the family of saturated nitrogen heterocycles. Although often challenging to synthesize, substituted azetidines strongly attract chemists because of their importance in catalysis, stereoselective synthesis and medicinal chemistry. This review aims to give a brief summary of modern developments in direct metal-based functionalization of the azetidine ring, focusing on the regio- and stereoselectivity of these reactions, as well as on some useful synthetic applications. It will be highlighted, in particular, how an interplay of factors such as structure, substitutions at both nitrogen and carbon atoms and coordinative phenomena deeply influence the reactivity of the corresponding metallated species, paving the way for easy planning a site-selective functionalization of azetidines.

Graphical abstract: Recent advances in the chemistry of metallated azetidines

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Publication details

The article was received on 02 Aug 2016, accepted on 13 Oct 2016 and first published on 13 Oct 2016


Article type: Review Article
DOI: 10.1039/C6OB01665K
Citation: Org. Biomol. Chem., 2017,15, 34-50
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    Recent advances in the chemistry of metallated azetidines

    D. Antermite, L. Degennaro and R. Luisi, Org. Biomol. Chem., 2017, 15, 34
    DOI: 10.1039/C6OB01665K

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