Chiral imidazolium prolinate salts as efficient synzymatic organocatalysts for the asymmetric aldol reaction
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comunitat-uji-handle3:10234/8639
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Title
Chiral imidazolium prolinate salts as efficient synzymatic organocatalysts for the asymmetric aldol reactionAuthor (s)
Date
2021-07-09Publisher
MDPIISSN
1420-3049Bibliographic citation
Porcar, Raúl, Eduardo García-Verdugo, Belén Altava, Maria I. Burguete, and Santiago V. Luis 2021. "Chiral Imidazolium Prolinate Salts as Efficient Synzymatic Organocatalysts for the Asymmetric Aldol Reaction" Molecules 26, no. 14: 4190Type
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Abstract
Chiral imidazolium l-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient ... [+]
Chiral imidazolium l-prolinate salts, providing a complex network of supramolecular interaction in a chiral environment, have been studied as synzymatic catalytic systems. They are demonstrated to be green and efficient chiral organocatalysts for direct asymmetric aldol reactions at room temperature. The corresponding aldol products were obtained with moderate to good enantioselectivities. The influence of the presence of chirality in both the imidazolium cation and the prolinate anion on the transfer of chirality from the organocatalyst to the aldol product has been studied. Moreover, interesting match/mismatch situations have been observed regarding configuration of chirality of the two components through the analysis of results for organocatalysts derived from both enantiomers of prolinate (R/S) and the trans/cis isomers for the chiral fragment of the cation. This is associated with differences in the corresponding reaction rates but also to the different tendencies for the formation of aggregates, as evidenced by nonlinear effects studies (NLE). Excellent activities, selectivities, and enantioselectivities could be achieved by an appropriate selection of the structural elements at the cation and anion. [-]
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Molecules, Volume 26, Issue 14 (2021)Funder Name
Ministerio de Ciencia, Innovación y Universidades | Universitat Jaume I
Project code
RTI2018-098233-B-C22 | UJI-B2019-40
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info:eu-repo/semantics/openAccess
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