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Metal-catalysed 1,2-diamination reactions

Nature Chemistry volume 1, pages 269–275 (2009)Cite this article

Abstract

The 1,2-diamine motif is present in a number of natural products with interesting biological activity and in many important pharmaceutical agents. Chiral 1,2-diamines are also widely used as the control elements in asymmetric synthesis and catalysis. Such compounds are thus an attractive target for the synthetic chemist. Although the diamination of an alkene seems an obvious route to these structures, far less research has been devoted to it than to the analogous dihydroxylation or aminohydroxylation reactions that are well-established processes in asymmetric synthesis. Here, we examine recent advances in metal-catalysed diamination reactions and their asymmetric variants. Given the prevalence of these structures, it seems likely that they will find extensive application in the construction of natural products and drug molecules in the near future.

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Figure 1: The ubiquity of the 1,2-diamine motif.
Figure 2: Diaminations of alkenes through three-component reactions.
Figure 3: Pd(II)- and Ni(II)-catalysed intramolecular diaminations of alkenes.
Figure 4: Metal-catalysed intermolecular diaminations of conjugated dienes.
Figure 5: Metal-catalysed intermolecular diaminations of terminal alkenes and related amination of esters.
Figure 6: Metal-catalysed asymmetric diaminations of conjugated dienes and terminal alkenes.

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Acknowledgements

Research conducted in the Goti laboratories was supported by the Ministry of Instruction, University and Research, Italy, and Ente Cassa di Risparmio di Firenze, Italy.

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  1. Department of Organic Chemistry “Ugo Schiff”, Laboratory of Design, Synthesis and Study of Biologically Active Heterocycles (HeteroBioLab), University of Florence, Via della Lastruccia 13, Sesto Fiorentino, I-50019, Italy

    Francesca Cardona & Andrea Goti

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  1. Francesca Cardona
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  2. Andrea Goti
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F.C. and A.G. contributed equally to this collaborative writing project.

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Correspondence to Andrea Goti.

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Cardona, F., Goti, A. Metal-catalysed 1,2-diamination reactions. Nature Chem 1, 269–275 (2009). https://doi.org/10.1038/nchem.256

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