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Issue 11, 2014
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Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes

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Abstract

The reactivity of triethylaluminum towards salicylaldimine sulfonamides was probed, affording well-defined complexes through consecutive protonolysis of two Al–C bonds by the proligand. These complexes, when combined with an achiral anilinic N-oxide, catalyze the asymmetric addition of trimethylsilylcyanide to a wide range of aldehydes, with good activity and enantioselectivity (up to 91% ee). Insertion of the benzaldehyde substrate into the Al–N amido bond was observed, bringing elements for discussion around the nature of the actual active species.

Graphical abstract: Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes

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Publication details

The article was received on 21 Nov 2013, accepted on 17 Dec 2013 and first published on 19 Dec 2013


Article type: Paper
DOI: 10.1039/C3DT53292E
Citation: Dalton Trans., 2014,43, 4530-4536
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    Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes

    J. Ternel, F. Agbossou-Niedercorn and R. M. Gauvin, Dalton Trans., 2014, 43, 4530
    DOI: 10.1039/C3DT53292E

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