Chiral phenoxyimino-amido aluminum complexes for the asymmetric cyanation of aldehydes
J Ternel1, F Agbossou-Niedercorn, R M Gauvin
1Université Lille Nord de France, France.
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.
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