Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media
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 asymmet...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English English |
| Published: |
Wiley-Blackwell
2013
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/30308/1/Various%20polar%20tripeptides%20as%20asymmetric%20organocatalyst%20in%20direct%20aldol%20reactions%20in%20aqueous%20media.pdf |
| _version_ | 1796971714928705536 |
|---|---|
| author | Bayat, Saadi Tejo, Bimo Ario Salleh, Abu Bakar Abd. Malek, Emilia Mohd Yahaya, Normi Abdul Rahman, Mohd Basyaruddin |
| author_facet | Bayat, Saadi Tejo, Bimo Ario Salleh, Abu Bakar Abd. Malek, Emilia Mohd Yahaya, Normi Abdul Rahman, Mohd Basyaruddin |
| author_sort | Bayat, Saadi |
| collection | UPM |
| description | 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. |
| first_indexed | 2024-03-06T08:17:10Z |
| format | Article |
| id | upm.eprints-30308 |
| institution | Universiti Putra Malaysia |
| language | English English |
| last_indexed | 2024-03-06T08:17:10Z |
| publishDate | 2013 |
| publisher | Wiley-Blackwell |
| record_format | dspace |
| spelling | upm.eprints-303082015-08-24T01:19:06Z http://psasir.upm.edu.my/id/eprint/30308/ Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media Bayat, Saadi Tejo, Bimo Ario Salleh, Abu Bakar Abd. Malek, Emilia Mohd Yahaya, Normi Abdul Rahman, Mohd Basyaruddin 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. Wiley-Blackwell 2013-11 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/30308/1/Various%20polar%20tripeptides%20as%20asymmetric%20organocatalyst%20in%20direct%20aldol%20reactions%20in%20aqueous%20media.pdf Bayat, Saadi and Tejo, Bimo Ario and Salleh, Abu Bakar and Abd. Malek, Emilia and Mohd Yahaya, Normi and Abdul Rahman, Mohd Basyaruddin (2013) Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media. Chirality, 25 (11). pp. 726-734. ISSN 0899-0042 10.1002/chir.22205 English |
| spellingShingle | Bayat, Saadi Tejo, Bimo Ario Salleh, Abu Bakar Abd. Malek, Emilia Mohd Yahaya, Normi Abdul Rahman, Mohd Basyaruddin Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title | Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title_full | Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title_fullStr | Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title_full_unstemmed | Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title_short | Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| title_sort | various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media |
| url | http://psasir.upm.edu.my/id/eprint/30308/1/Various%20polar%20tripeptides%20as%20asymmetric%20organocatalyst%20in%20direct%20aldol%20reactions%20in%20aqueous%20media.pdf |
| work_keys_str_mv | AT bayatsaadi variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia AT tejobimoario variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia AT sallehabubakar variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia AT abdmalekemilia variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia AT mohdyahayanormi variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia AT abdulrahmanmohdbasyaruddin variouspolartripeptidesasasymmetricorganocatalystindirectaldolreactionsinaqueousmedia |