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Various Polar Tripeptides as Asymmetric Organocatalyst in Direct Aldol Reactions in Aqueous Media
Author(s) -
Bayat Saadi,
Tejo Bimo A.,
Salleh Abu Bakar,
Abdmalek Emilia,
Normi Yahaya M.,
Rahman Mohd Basyaruddin Abdul
Publication year - 2013
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22205
Subject(s) - chemistry , aldol reaction , polar , tripeptide , aqueous medium , organocatalysis , aqueous solution , organic chemistry , enantioselective synthesis , combinatorial chemistry , catalysis , amino acid , biochemistry , physics , astronomy
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. Chirality 25:726–734, 2013 . © 2013 Wiley Periodicals, Inc