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Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media.
Chirality. 2013 Nov; 25(11):726-34.C

Abstract

A series of tripeptide organocatalysts containing a secondary amine group and two amino acids with polar side chain units were developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The effectiveness of short polar peptides as asymmetric catalysts in aldol reactions to attain high yields of enantio- and diastereoselective isomers were investigated. In a comparison, glutamic acid and histidine produced higher % ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric aldol addition reaction in aqueous media.

Authors+Show Affiliations

Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang, Selangor, Malaysia.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23966316

Citation

Bayat, Saadi, et al. "Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media." Chirality, vol. 25, no. 11, 2013, pp. 726-34.
Bayat S, Tejo BA, Salleh AB, et al. Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media. Chirality. 2013;25(11):726-34.
Bayat, S., Tejo, B. A., Salleh, A. B., Abdmalek, E., Normi, Y. M., & Abdul Rahman, M. B. (2013). Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media. Chirality, 25(11), 726-34. https://doi.org/10.1002/chir.22205
Bayat S, et al. Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media. Chirality. 2013;25(11):726-34. PubMed PMID: 23966316.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media. AU - Bayat,Saadi, AU - Tejo,Bimo A, AU - Salleh,Abu Bakar, AU - Abdmalek,Emilia, AU - Normi,Yahaya M, AU - Abdul Rahman,Mohd Basyaruddin, Y1 - 2013/08/22/ PY - 2013/04/27/received PY - 2013/05/24/revised PY - 2013/05/29/accepted PY - 2013/8/23/entrez PY - 2013/8/24/pubmed PY - 2014/5/23/medline KW - Aldol reaction, asymmetric KW - organocatalyst KW - short polar peptide SP - 726 EP - 34 JF - Chirality JO - Chirality VL - 25 IS - 11 N2 - A series of tripeptide organocatalysts containing a secondary amine group and two amino acids with polar side chain units were developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The effectiveness of short polar peptides as asymmetric catalysts in aldol reactions to attain high yields of enantio- and diastereoselective isomers were investigated. In a comparison, glutamic acid and histidine produced higher % ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric aldol addition reaction in aqueous media. SN - 1520-636X UR - https://www.unboundmedicine.com/medline/citation/23966316/Various_polar_tripeptides_as_asymmetric_organocatalyst_in_direct_aldol_reactions_in_aqueous_media_ L2 - https://doi.org/10.1002/chir.22205 DB - PRIME DP - Unbound Medicine ER -