Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions
Taking advantage of the excellent dissolution ability of ionic liquids, which can also dissolve DNA and hydrophobic compounds, we investigated the homogeneous asymmetric Diels-Alder reaction using DNA, a natural chiral source, and porphyrin copper(II) complexes as asymmetric catalysts in ionic liqui...
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| Format: | Article |
| Language: | English |
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Elsevier
2025-12-01
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| Series: | Journal of Ionic Liquids |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2772422025000382 |
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| author | Kaoru Nobuoka Kensuke Sumi Satoshi Kitaoka |
| author_facet | Kaoru Nobuoka Kensuke Sumi Satoshi Kitaoka |
| author_sort | Kaoru Nobuoka |
| collection | DOAJ |
| description | Taking advantage of the excellent dissolution ability of ionic liquids, which can also dissolve DNA and hydrophobic compounds, we investigated the homogeneous asymmetric Diels-Alder reaction using DNA, a natural chiral source, and porphyrin copper(II) complexes as asymmetric catalysts in ionic liquid solutions. In [N4444][Gly], the reaction substrates were phase-separated, and the reaction mixture gelled or solidified at low temperatures, resulting in ineffective asymmetric catalysis. However, the reaction proceeded in a homogeneous system in 75 % [N1223][N(CN)2], which is not possible in water alone, and high yield, diastereoselectivity, and enantioselectivity were obtained at -20 °C. The utilization of ionic liquids as solvents would not only enable homogeneous reactions, but also reactions at low temperatures, and would be a powerful tool for high stereoselectivity in DNA-organometallic-catalyzed asymmetric reactions. |
| format | Article |
| id | doaj-art-cead2ea110164a2aa930550c51b4d2e0 |
| institution | Kabale University |
| issn | 2772-4220 |
| language | English |
| publishDate | 2025-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Ionic Liquids |
| spelling | doaj-art-cead2ea110164a2aa930550c51b4d2e02025-08-20T03:44:25ZengElsevierJournal of Ionic Liquids2772-42202025-12-015210016910.1016/j.jil.2025.100169Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutionsKaoru Nobuoka0Kensuke Sumi1Satoshi Kitaoka2Department of Science and Technology, Faculty of Science and Technology, Oita University, 700 Dannoharu, Oita, Japan; Corresponding authors.Division of Applied Chemistry, Graduate School of Engineering, Oita University, 700 Dannoharu, Oita, JapanDepartment of Biotechnology and Chemistry, Faculty of Engineering, Kindai University, 1 Takaya Umenobe, Higashi-Hiroshima, Japan; Corresponding authors.Taking advantage of the excellent dissolution ability of ionic liquids, which can also dissolve DNA and hydrophobic compounds, we investigated the homogeneous asymmetric Diels-Alder reaction using DNA, a natural chiral source, and porphyrin copper(II) complexes as asymmetric catalysts in ionic liquid solutions. In [N4444][Gly], the reaction substrates were phase-separated, and the reaction mixture gelled or solidified at low temperatures, resulting in ineffective asymmetric catalysis. However, the reaction proceeded in a homogeneous system in 75 % [N1223][N(CN)2], which is not possible in water alone, and high yield, diastereoselectivity, and enantioselectivity were obtained at -20 °C. The utilization of ionic liquids as solvents would not only enable homogeneous reactions, but also reactions at low temperatures, and would be a powerful tool for high stereoselectivity in DNA-organometallic-catalyzed asymmetric reactions.http://www.sciencedirect.com/science/article/pii/S2772422025000382Ionic liquidsDNAPorphyrinAsymmetric catalystDiels-Alder reaction |
| spellingShingle | Kaoru Nobuoka Kensuke Sumi Satoshi Kitaoka Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions Journal of Ionic Liquids Ionic liquids DNA Porphyrin Asymmetric catalyst Diels-Alder reaction |
| title | Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions |
| title_full | Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions |
| title_fullStr | Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions |
| title_full_unstemmed | Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions |
| title_short | Homogeneous asymmetric Diels-Alder reaction using copper(II) porphyrin-DNA complexes as asymmetric catalysts in ionic liquid solutions |
| title_sort | homogeneous asymmetric diels alder reaction using copper ii porphyrin dna complexes as asymmetric catalysts in ionic liquid solutions |
| topic | Ionic liquids DNA Porphyrin Asymmetric catalyst Diels-Alder reaction |
| url | http://www.sciencedirect.com/science/article/pii/S2772422025000382 |
| work_keys_str_mv | AT kaorunobuoka homogeneousasymmetricdielsalderreactionusingcopperiiporphyrindnacomplexesasasymmetriccatalystsinionicliquidsolutions AT kensukesumi homogeneousasymmetricdielsalderreactionusingcopperiiporphyrindnacomplexesasasymmetriccatalystsinionicliquidsolutions AT satoshikitaoka homogeneousasymmetricdielsalderreactionusingcopperiiporphyrindnacomplexesasasymmetriccatalystsinionicliquidsolutions |