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"We explored the natural amino acid L-proline to be catalysts for the direct asymmetric Mannich-type reaction of acetone with a variety of preformed aldimines derived from o-anisidine. In the first part of this project, we explored the direct asymmetric Mannich-type reaction between acetone and N-(p-nitrobenzylidene)Aniline, in the presence of 30 mol % of L-proline.N-(p-nitrobenzylidene)Aniline was the intermediate compound which made between Aniline and 4-nitrobenzaldehyde.The reaction was set under normal condition and room temperature. We got 2 conformation products. Detail characterization of two products was determined by TLC, Column Chromatography, NMR, and HPLC. The percent yield of main product was 67.5%, and the published value was 52%. In the second part of this project, we explored the same asymmetric Mannich-type reaction using p-Anisaldehyde instead of 4-nitrobenzaldehyde. We got an unknown compound, and we could not identify the structure of this compound until we get mass spectrum. In the third part of this project, we explored one-pot three-component reaction between acetone, Aniline, and p-Anisaldehyde in the presence of 30 mol % of L-proline. We got 2 conformation products too, but the ratio of major and minor conformers is switched."
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"2015 December 23"
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"Zhang, Xiaoqiao (Kerry Zhang)",
"Ghosh, Phalguni",
"Lavey, Brian",
"Middlesex College, Department of Natural Sciences"
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