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Chiral Room Temperature Ionic Liquids as Enantioselective Promoters for the Asymmetric Aldol Reaction
Author(s) -
González Laura,
Escorihuela Jorge,
Altava Belén,
Burguete M. Isabel,
Luis Santiago V.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402436
Subject(s) - aldol reaction , chemistry , enantioselective synthesis , ionic liquid , catalysis , chirality (physics) , proline , enantiomer , organocatalysis , aldol condensation , combinatorial chemistry , organic chemistry , amino acid , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
Chiral ionic liquids derived from natural amino acids are shown to be green and efficient media for direct asymmetric aldol reactions at room temperature catalyzed by ( S )‐proline. The corresponding aldol products were obtained with moderate to good enantioselectivities. A transfer of chirality from the chiral reaction media has been observed as well as the participation of match/mismatch interactions of the chiral medium with both enantiomers of proline. Moreover, these catalytic systems were easily recovered by simple filtration, and studies on their reuse have demonstrated that recycling is possible for at least four runs with only a slight reduction in activity.