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- W2092483886 abstract "Asymmetric reduction of N-aryl ketimines 1a–k, 43, and 45 with trichlorosilane can be catalyzed by new N-methyl l-amino acid-derived Lewis-basic organocatalysts, such as the valine-derived bisamide 3d (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure–reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i-Pr vs Me, as in 3d and 6e), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene–arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology." @default.
- W2092483886 created "2016-06-24" @default.
- W2092483886 creator A5015474948 @default.
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- W2092483886 creator A5084478574 @default.
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- W2092483886 date "2006-01-01" @default.
- W2092483886 modified "2023-10-17" @default.
- W2092483886 title "Formamides derived from N-methyl amino acids serve as new chiral organocatalysts in the enantioselective reduction of aromatic ketimines with trichlorosilane" @default.
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- W2092483886 doi "https://doi.org/10.1016/j.tet.2005.08.117" @default.
- W2092483886 hasPublicationYear "2006" @default.
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