Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water
New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-c...
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| Format: | Article |
| Language: | English |
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Slovenian Chemical Society
2020-12-01
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| Series: | Acta Chimica Slovenica |
| Subjects: | |
| Online Access: | https://journals.matheo.si/index.php/ACSi/article/view/4748 |
| _version_ | 1819320254153621504 |
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| author | Elif Keskin Cigdem Yolacan Feray Aydogan |
| author_facet | Elif Keskin Cigdem Yolacan Feray Aydogan |
| author_sort | Elif Keskin |
| collection | DOAJ |
| description | New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed. |
| first_indexed | 2024-12-24T11:16:39Z |
| format | Article |
| id | doaj.art-85ff6b876d434742823420a66880eb12 |
| institution | Directory Open Access Journal |
| issn | 1318-0207 1580-3155 |
| language | English |
| last_indexed | 2024-12-24T11:16:39Z |
| publishDate | 2020-12-01 |
| publisher | Slovenian Chemical Society |
| record_format | Article |
| series | Acta Chimica Slovenica |
| spelling | doaj.art-85ff6b876d434742823420a66880eb122022-12-21T16:58:21ZengSlovenian Chemical SocietyActa Chimica Slovenica1318-02071580-31552020-12-016741014102310.17344/acsi.2018.4748914Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in WaterElif Keskin0Cigdem Yolacan1Feray Aydogan2Yildiz Technical UniversityYildiz Technical UniversityYildiz Technical UniversityNew di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed.https://journals.matheo.si/index.php/ACSi/article/view/4748aldol reactionorganocatalysisasymmetric synthesisprolinamide |
| spellingShingle | Elif Keskin Cigdem Yolacan Feray Aydogan Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water Acta Chimica Slovenica aldol reaction organocatalysis asymmetric synthesis prolinamide |
| title | Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water |
| title_full | Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water |
| title_fullStr | Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water |
| title_full_unstemmed | Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water |
| title_short | Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water |
| title_sort | synthesis of new di and triamides as potential organocatalysts for asymmetric aldol reaction in water |
| topic | aldol reaction organocatalysis asymmetric synthesis prolinamide |
| url | https://journals.matheo.si/index.php/ACSi/article/view/4748 |
| work_keys_str_mv | AT elifkeskin synthesisofnewdiandtriamidesaspotentialorganocatalystsforasymmetricaldolreactioninwater AT cigdemyolacan synthesisofnewdiandtriamidesaspotentialorganocatalystsforasymmetricaldolreactioninwater AT ferayaydogan synthesisofnewdiandtriamidesaspotentialorganocatalystsforasymmetricaldolreactioninwater |