Amine-Catalyzed Direct Asymmetric Mannich Reaction

Material Information

Title:
Amine-Catalyzed Direct Asymmetric Mannich Reaction
Series Title:
Student Symposium 2015
Creator:
Zhang, Xiaoqiao (Kerry Zhang) ( Author, Primary )
Ghosh, Phalguni ( Advisor )
Lavey, Brian ( Advisor )
Middlesex College, Department of Natural Sciences ( Sponsor )
Place of Publication:
Edison, NJ
Publisher:
Middlesex College
Publication Date:

Subjects

Subjects / Keywords:
College students -- poster presentations ( lcsh )
Student Works -- Natural Sciences -- poster presentations ( lcsh )
Chemistry ( lcsh )
Student works -- Natural Sciences -- academic theses ( lcsh )
Middlesex College (Edison, NJ) -- Student works
Middlesex County College (Edison, NJ) ( lcsh )
Temporal Coverage:
Academic Year 2015-2016 ( 2015 - 2016 )
Spatial Coverage:
New Jersey -- Edison

Notes

Abstract:
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.

Record Information

Source Institution:
Middlesex County College Institution
Holding Location:
Middlesex County College Institution
Rights Management:
All applicable rights reserved by the source institution and holding location.

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