The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline
Michael addition reactions of n-pentanal with ß-nitrostyrene in achiral and chiral ionic liquids catalyzed by l-proline were studied. Results indicate anion plays an important role as weak coordination properties in the reactivity and stereoselectivity towards Michael product. 1-Butyl-3-methylimidaz...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Wiley-VCH Verlag
2019
|
| Online Access: | http://psasir.upm.edu.my/id/eprint/82592/ http://psasir.upm.edu.my/id/eprint/82592/1/The%20role%20of%20neutral.pdf |
| _version_ | 1848859310684110848 |
|---|---|
| author | M. Omar, Emmy A. Rahman, Mohd Basyaruddin Ni, Bukuo Headley, Allan D. |
| author_facet | M. Omar, Emmy A. Rahman, Mohd Basyaruddin Ni, Bukuo Headley, Allan D. |
| author_sort | M. Omar, Emmy |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | Michael addition reactions of n-pentanal with ß-nitrostyrene in achiral and chiral ionic liquids catalyzed by l-proline were studied. Results indicate anion plays an important role as weak coordination properties in the reactivity and stereoselectivity towards Michael product. 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Bmim][NTf2]) ionic liquid was found to be the best solvent media with a high yield (up to 90%) and a high diastereomeric ratio (syn/anti: 91/9), with moderate enantioselectivity (38% ee) among ten ionic liquids tested. The ionic liquid has been reusable over five numbers of cycles. |
| first_indexed | 2025-11-15T12:27:19Z |
| format | Article |
| id | upm-82592 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T12:27:19Z |
| publishDate | 2019 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-825922020-10-17T21:37:09Z http://psasir.upm.edu.my/id/eprint/82592/ The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline M. Omar, Emmy A. Rahman, Mohd Basyaruddin Ni, Bukuo Headley, Allan D. Michael addition reactions of n-pentanal with ß-nitrostyrene in achiral and chiral ionic liquids catalyzed by l-proline were studied. Results indicate anion plays an important role as weak coordination properties in the reactivity and stereoselectivity towards Michael product. 1-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([Bmim][NTf2]) ionic liquid was found to be the best solvent media with a high yield (up to 90%) and a high diastereomeric ratio (syn/anti: 91/9), with moderate enantioselectivity (38% ee) among ten ionic liquids tested. The ionic liquid has been reusable over five numbers of cycles. Wiley-VCH Verlag 2019 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/82592/1/The%20role%20of%20neutral.pdf M. Omar, Emmy and A. Rahman, Mohd Basyaruddin and Ni, Bukuo and Headley, Allan D. (2019) The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline. Advanced Energy Materials, 49 (12). pp. 1578-1591. ISSN 1614-6832; ESSN: 1614-6840 10.1080/00397911.2019.1604969 |
| spellingShingle | M. Omar, Emmy A. Rahman, Mohd Basyaruddin Ni, Bukuo Headley, Allan D. The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title | The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title_full | The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title_fullStr | The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title_full_unstemmed | The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title_short | The role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric Michael addition reaction of n-pentanal with B-nitrostryrene catalyzed by L-Proline |
| title_sort | role of neutral anions in ionic liquid as solvent media for the reactivity and stereoselectivity towards asymmetric michael addition reaction of n-pentanal with b-nitrostryrene catalyzed by l-proline |
| url | http://psasir.upm.edu.my/id/eprint/82592/ http://psasir.upm.edu.my/id/eprint/82592/ http://psasir.upm.edu.my/id/eprint/82592/1/The%20role%20of%20neutral.pdf |