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Issue 21, 2011
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Nitrogen cation–π interactions in asymmetric organocatalytic synthesis

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Cation–π interactions have been widely exploited and utilised in the structural biology arena, their fundamental importance in supramolecular chemistry and the pivotal role they play in host guest chemistry has rapidly expanded. In terms of organic synthesis π–π, CH–π and cation–π interactions are often invoked providing hypotheses for observed selectivities and reaction outcomes although fundamental studies of these interactions are less well reported, especially in the organic synthesis arena. This article considers cation–π interactions in the field of asymmetric organocatalysis and provides a summary of cases where such interactions may play an important role. Importantly this article sets out to highlight where such interactions could be operating in order to highlight the potential wealth of investigations to be had in this area rather than categorically claiming such interactions are in operation. For asymmetric catalysis this is particularly important as the geometry of a transition state dictates the stereochemical outcome of the reaction, this article provides a perspective on such phenomena.

Graphical abstract: Nitrogen cation–π interactions in asymmetric organocatalytic synthesis

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The article was received on 13 Feb 2011, accepted on 19 Apr 2011 and first published on 16 Jun 2011

Article type: Perspective
DOI: 10.1039/C1OB05228D
Org. Biomol. Chem., 2011,9, 7275-7281

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    Nitrogen cation–π interactions in asymmetric organocatalytic synthesis

    S. Yamada and J. S. Fossey, Org. Biomol. Chem., 2011, 9, 7275
    DOI: 10.1039/C1OB05228D

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