Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions
By varying the steric and electronic surroundings of the hydrogen-bonding motif, the novel chiral <i>Cinchona</i>-alkaloid based selenoureas were developed. Acting as bifunctional catalysts, they were applied in the Michael reactions of dithiomalonate and nitrostyrene providing chiral ad...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/23/7303 |
| _version_ | 1827674782019092480 |
|---|---|
| author | Mariola Zielińska-Błajet Żaneta A. Mała Rafał Kowalczyk |
| author_facet | Mariola Zielińska-Błajet Żaneta A. Mała Rafał Kowalczyk |
| author_sort | Mariola Zielińska-Błajet |
| collection | DOAJ |
| description | By varying the steric and electronic surroundings of the hydrogen-bonding motif, the novel chiral <i>Cinchona</i>-alkaloid based selenoureas were developed. Acting as bifunctional catalysts, they were applied in the Michael reactions of dithiomalonate and nitrostyrene providing chiral adducts with up to 96% ee. The asymmetric Michael–-hemiacetalization reaction of benzylidene pyruvate and dimedone, performed with the assistance of 5 mol% of selenoureas, furnished the product with up to 93% ee and excellent yields. The effectiveness of the new hydrogen-bond donors was also proved in solvent-free reactions under ball mill conditions, supporting the sustainability of the devised catalytic protocol. |
| first_indexed | 2024-03-10T04:47:05Z |
| format | Article |
| id | doaj.art-22f04c0a4bea4632a2aaa61205cd3635 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T04:47:05Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-22f04c0a4bea4632a2aaa61205cd36352023-11-23T02:50:28ZengMDPI AGMolecules1420-30492021-12-012623730310.3390/molecules26237303Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free ConditionsMariola Zielińska-Błajet0Żaneta A. Mała1Rafał Kowalczyk2Faculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandFaculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandFaculty of Chemistry, Wrocław University of Science and Technology, Wybrzeże Wyspiańskiego 27, 50-370 Wrocław, PolandBy varying the steric and electronic surroundings of the hydrogen-bonding motif, the novel chiral <i>Cinchona</i>-alkaloid based selenoureas were developed. Acting as bifunctional catalysts, they were applied in the Michael reactions of dithiomalonate and nitrostyrene providing chiral adducts with up to 96% ee. The asymmetric Michael–-hemiacetalization reaction of benzylidene pyruvate and dimedone, performed with the assistance of 5 mol% of selenoureas, furnished the product with up to 93% ee and excellent yields. The effectiveness of the new hydrogen-bond donors was also proved in solvent-free reactions under ball mill conditions, supporting the sustainability of the devised catalytic protocol.https://www.mdpi.com/1420-3049/26/23/7303<i>Cinchona</i> alkaloidsselenoureashydrogen-bondingMichael additionball-millingorganocatalysis |
| spellingShingle | Mariola Zielińska-Błajet Żaneta A. Mała Rafał Kowalczyk Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions Molecules <i>Cinchona</i> alkaloids selenoureas hydrogen-bonding Michael addition ball-milling organocatalysis |
| title | Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions |
| title_full | Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions |
| title_fullStr | Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions |
| title_full_unstemmed | Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions |
| title_short | Efficacy of Selenourea Organocatalysts in Asymmetric Michael Reactions under Standard and Solvent-Free Conditions |
| title_sort | efficacy of selenourea organocatalysts in asymmetric michael reactions under standard and solvent free conditions |
| topic | <i>Cinchona</i> alkaloids selenoureas hydrogen-bonding Michael addition ball-milling organocatalysis |
| url | https://www.mdpi.com/1420-3049/26/23/7303 |
| work_keys_str_mv | AT mariolazielinskabłajet efficacyofselenoureaorganocatalystsinasymmetricmichaelreactionsunderstandardandsolventfreeconditions AT zanetaamała efficacyofselenoureaorganocatalystsinasymmetricmichaelreactionsunderstandardandsolventfreeconditions AT rafałkowalczyk efficacyofselenoureaorganocatalystsinasymmetricmichaelreactionsunderstandardandsolventfreeconditions |