Histidine-based salt as an ionic tag for proline: application in enantioselective cross aldol reaction in ionic liquids

A new ionic-liquid supported aminocatalyst was synthesized by the peptide coupling of proline on a ring-dialkylated histidine salt serving as ionic support. The catalytic activity and enantioselectivity of the obtained dipeptide catalyst were evaluated in the enantioselective cross aldol reaction of...

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Bibliographic Details
Published inSynthetic communications Vol. 50; no. 10; pp. 1512 - 1522
Main Authors Kui, Tony, Guillen, Frédéric
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis 18.05.2020
Taylor & Francis Ltd
Taylor & Francis: STM, Behavioural Science and Public Health Titles
Subjects
Acetone
Aldehydes
Benzaldehyde
Catalysts
Catalytic activity
Chemical Sciences
Chemistry
Chemistry, Organic
Enantiomers
Enantioselective aldol reaction
Histidine
Ionic liquids
ionic support
Ions
Physical Sciences
Proline
Science & Technology
Solvents
Supported organocatalysis
proline
DESIGN
ORGANOCATALYSTS
PEPTIDES
ionic support
ACETONE
Enantioselective aldol reaction
Supported organocatalysis
CHIRAL AMINO-ACID
HIGHLY EFFICIENT
MICHAEL ADDITION
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Summary:A new ionic-liquid supported aminocatalyst was synthesized by the peptide coupling of proline on a ring-dialkylated histidine salt serving as ionic support. The catalytic activity and enantioselectivity of the obtained dipeptide catalyst were evaluated in the enantioselective cross aldol reaction of substituted benzaldehyde derivatives with acetone, in organic solvent and in ionic liquids, and both were found to be significantly higher in ionic liquids than in organic solvents. The [bmim][OTf] - catalyst system could be recycled for up to five cycles without any loss in activity.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2020.1745241