Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction

Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction Several amino acids and their derivatives have been evaluated as organic catalysts for the nitroaldol reaction. It was found that when an unprotected amino group and an unprotected carboxylate group were present in the organocatalyst, both the nitroaldol reaction and subsequent elimination could occur to afford nitroalkenes from aromatic aldehydes and nitromethane. The best results were obtained by use of γ-amino acids derived from l-glutamine. It is suggested that the amino group is important for intermediate Schiff base formation and that the free carboxylate group facilitates the elimination step. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Catalyst functional group cooperativity in the amino acid-catalysed nitroaldol condensation reaction

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Publisher
Springer Journals
Copyright
Copyright © 2012 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-012-0853-x
Publisher site
See Article on Publisher Site

Abstract

Several amino acids and their derivatives have been evaluated as organic catalysts for the nitroaldol reaction. It was found that when an unprotected amino group and an unprotected carboxylate group were present in the organocatalyst, both the nitroaldol reaction and subsequent elimination could occur to afford nitroalkenes from aromatic aldehydes and nitromethane. The best results were obtained by use of γ-amino acids derived from l-glutamine. It is suggested that the amino group is important for intermediate Schiff base formation and that the free carboxylate group facilitates the elimination step.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Oct 19, 2012

References

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