Davanagere, PM and De, M and Chanda, K and Maiti, B (2023) Diastereo- and Enantioselective Synthesis of Highly Functionalized Tetrahydropyridines by Recyclable Novel Bifunctional C2-Symmetric Ionic Liquid–Supported (S)-Proline Organocatalyst. In: Catalysts, 13 (1).
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Abstract
An efficient, novel bifunctional C2-symmetric ionic liquid–supported (S)-proline organocatalyst 7 was developed for a one-pot, five-component reaction involving β-keto esters 8, aryl aldehydes 9, and aryl amines 10, affording highly functionalized tetrahydropyridines 11a–o by simultaneous generation of fives bonds and two stereogenic centers with extraordinary diastereo- and enantioselectivities (up to >99:1 dr, 95:5 er) in isopropanol with high yields (up to 92%). This protocol provides quick access to diverse enantio-enriched, highly functionalized diastereo- and enantioselective tetrahydropyridines in a green medium without any column chromatographic purification. The catalyst was recycled five times without significant loss of its catalytic activity.
| Item Type: | Journal Article |
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| Publication: | Catalysts |
| Publisher: | MDPI |
| Additional Information: | The copyright for this article belongs to the Authors. |
| Keywords: | asymmetric catalysis; functionalized tetrahydropyridines; multicomponent reactions; stereoselectivities |
| Department/Centre: | Division of Chemical Sciences > Organic Chemistry |
| Date Deposited: | 16 Feb 2023 05:30 |
| Last Modified: | 16 Feb 2023 05:30 |
| URI: | https://eprints.iisc.ac.in/id/eprint/80315 |
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