l-proline and l-histidine co-catalyzed Baylis–Hillman reaction

l-proline and l-histidine co-catalyzed Baylis–Hillman reaction Baylis–Hillman reaction between an aldehyde and an activated alkene, such as alkyl vinyl ketones, acrylates, acrylonitrile, and vinylsulfones, giving the β-hydroxy-α-methylene carbonyl compounds, is a versatile and atom-economical carbon–carbon bond-forming reaction. This reaction usually is catalyzed by strong Lewis bases such as tertiary amines and suffers from slow reaction rate. In this paper the Baylis–Hillman reaction between arylaldehydes and methyl vinyl ketone was successfully realized by a catalytic amount of l-proline and l-histidine system to give the corresponding normal Baylis–Hillman adducts in moderate to high yields for the first time. The effects of solvent and reagent electro property on the yields of this reaction were also investigated. Proline and histidine are naturally widely present amino acids in food system; furthermore, aldehydes and activated alkenes can also be easily produced in food processing, so proline and histidine co-catalyzed Baylis–Hillman reaction may find application in explaining some phenomena in food processing. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

l-proline and l-histidine co-catalyzed Baylis–Hillman reaction

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Publisher
Springer Netherlands
Copyright
Copyright © 2011 by Springer Science+Business Media B.V.
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-011-0403-y
Publisher site
See Article on Publisher Site

Abstract

Baylis–Hillman reaction between an aldehyde and an activated alkene, such as alkyl vinyl ketones, acrylates, acrylonitrile, and vinylsulfones, giving the β-hydroxy-α-methylene carbonyl compounds, is a versatile and atom-economical carbon–carbon bond-forming reaction. This reaction usually is catalyzed by strong Lewis bases such as tertiary amines and suffers from slow reaction rate. In this paper the Baylis–Hillman reaction between arylaldehydes and methyl vinyl ketone was successfully realized by a catalytic amount of l-proline and l-histidine system to give the corresponding normal Baylis–Hillman adducts in moderate to high yields for the first time. The effects of solvent and reagent electro property on the yields of this reaction were also investigated. Proline and histidine are naturally widely present amino acids in food system; furthermore, aldehydes and activated alkenes can also be easily produced in food processing, so proline and histidine co-catalyzed Baylis–Hillman reaction may find application in explaining some phenomena in food processing.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Sep 15, 2011

References

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