N-Prolinylanthranilic acid derivatives as bifunctional organocatalysts for asymmetric aldol reactions |
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Authors: | Anthony J Pearson Santanu Panda |
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Institution: | Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA |
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Abstract: | Several N-prolinylanthranilic acid derivatives were prepared and tested as bifunctional organocatalysts in the direct asymmetric aldol reaction of cyclohexanone with p-nitrobenzaldehyde. It was found that methyl substitution ortho to the carboxylic acid improves enantioselectivity, but substitution ortho to the anilide group does not. The catalyst derived from 2-amino-6-methylbenzoic acid was tested over a range of direct asymmetric aldol reactions and its overall performance is equal to or better than many of the known prolinamide catalysts in terms of yield, diastereoselectivity, and enantioselectivity. |
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Keywords: | Asymmetric aldol reaction Organocatalysis Prolinamide Anthranilic acid |
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