Ion-tagged prolinamide organocatalysts for the direct aldol reaction on-water
Data(s) |
01/01/2016
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Resumo |
A concise synthesis of two imidazolium ion-tagged prolinamide organocatalysts 3 and 4, varying in anionic component (CF3COO- and PF6 -, respectively) is presented. The latter could be classified as an ionic liquid with a melting point of 66.3 °C, and glass transition temperature of 14.5 °C. The efficiency of each catalyst was compared via a direct aldol reaction revealing a large contrast in catalytic performance, with the catalyst bearing the PF6 - anion being superior. The optimal conditions were determined to be an on-water reaction system, and substrate scoping gave a range of desired aldol products in high conversion (up to >99 %), dr (up to 98:2), and er (up to 96:4). The application of these catalysts to beta-nitrostyrene conjugate addition is also presented. Graphical Abstract: [Figure not available: see fulltext.] |
Identificador | |
Idioma(s) |
eng |
Publicador |
Springer |
Relação |
http://dro.deakin.edu.au/eserv/DU:30083336/eyckens-iontagged-2016.pdf http://www.dx.doi.org/10.1007/s10562-015-1630-4 |
Direitos |
2016, Springer |
Palavras-Chave | #Science & Technology #Physical Sciences #Chemistry, Physical #Chemistry #Organocatalyst #Imidazolium #Aldol #Onwater #HIGHLY EFFICIENT ORGANOCATALYSTS #ASYMMETRIC MICHAEL REACTIONS #AQUEOUS-MEDIA #BIFUNCTIONAL ORGANOCATALYSTS #RECOVERABLE ORGANOCATALYSTS #ADDITION-REACTIONS #LIQUID #CATALYSIS #KETONES #NITROSTYRENES |
Tipo |
Journal Article |