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Issue 5, 2011
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Syntheses and transformations of α-azido ketones and related derivatives

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Abstract

Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C–C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

Graphical abstract: Syntheses and transformations of α-azido ketones and related derivatives

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Publication details

The article was received on 03 Sep 2010, accepted on 09 Dec 2010 and first published on 17 Feb 2011


Article type: Critical Review
DOI: 10.1039/C0CS00101E
Chem. Soc. Rev., 2011,40, 2797-2847

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    Syntheses and transformations of α-azido ketones and related derivatives

    T. Patonay, K. Kónya and É. Juhász-Tóth, Chem. Soc. Rev., 2011, 40, 2797
    DOI: 10.1039/C0CS00101E

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