The Use of Amino Acid L-Prolineas Catalyst forDirect Asymmetric Aldol Reactions

Material Information

Title:
The Use of Amino Acid L-Prolineas Catalyst forDirect Asymmetric Aldol Reactions
Series Title:
Student Symposium 2014
Creator:
Tran, Tram ( Author, Primary )
Ghosh, Phalguni ( 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 2014-2015 ( 2014 - 2015 )
Spatial Coverage:
New Jersey -- Edison

Notes

Abstract:
I have explored the asymmetric aldol reaction using natural amino acid L-proline as the catalyst. Amino acid L-Proline mimics class I aldolase enzyme to drive the aldol reaction through enamine-based mechanism. The use of catalyst L-Proline is the first example of amine-based asymmetric class I aldolase mimics. In the first part of this project, weexplored the direct asymmetric aldol reaction between acetone and 4-nitrobenzaldehyde in the presence of 30 mol % of L-proline.The reaction was set at room temperature under normal condition, and we got 2 products: aldol and α,β-unsaturated ketone product. Detail characterization of the two products was done using TLC, Column Chromatography, NMR and IR. The percent yield of asymmetric aldol product was 70% which is comparable to the published value of 68%. The yield of α,β-unsaturated ketone was10.5%. Further in the project, we explored the same aldol reaction using p-Anisaldehyde in place of 4-nitrobenzaldehyde. Only one product was obtained, and the exclusive product was α,β-unsaturated ketone instead of the expected asymmetric aldol product

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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