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Issue 71, 2013
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Atroposelective [2+2+2] cycloadditions catalyzed by a rhodium(i)–chiral phosphate system

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Enantioselective cationic Rh(I)-catalyzed [2+2+2] cycloaddition reactions between diynes and isocyanates relying on the chiral anion strategy have been devised. In the presence of [Rh(cod)Cl]2, 1,4-bis(diphenylphosphino)butane, and the silver phosphate salt Ag(S)–TRIP as the unique source of chirality, axially chiral pyridones were isolated with ees up to 82%. This approach is novel in the field of chiral anion-mediated asymmetric catalysis since atroposelective transformations have so far remained unprecedented. It also proves to be complementary to the classical strategy based on chiral L-type ligands.

Graphical abstract: Atroposelective [2+2+2] cycloadditions catalyzed by a rhodium(i)–chiral phosphate system

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The article was received on 30 Apr 2013, accepted on 26 Jun 2013 and first published on 27 Jun 2013

Article type: Communication
DOI: 10.1039/C3CC43188F
Chem. Commun., 2013,49, 7833-7835

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    Atroposelective [2+2+2] cycloadditions catalyzed by a rhodium(I)–chiral phosphate system

    M. Augé, M. Barbazanges, A. T. Tran, A. Simonneau, P. Elley, H. Amouri, C. Aubert, L. Fensterbank, V. Gandon, M. Malacria, J. Moussa and C. Ollivier, Chem. Commun., 2013, 49, 7833
    DOI: 10.1039/C3CC43188F

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