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- Title
Diastereo- and Enantioselective Synthesis of Highly Functionalized Tetrahydropyridines by Recyclable Novel Bifunctional C 2 -Symmetric Ionic Liquid–Supported (S)-Proline Organocatalyst.
- Authors
Davanagere, Prabhakara Madivalappa; De, Mrinmoy; Chanda, Kaushik; Maiti, Barnali
- 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.
- Subjects
AROMATIC amines; CATALYSTS recycling; CATALYTIC activity; PROLINE; NITROALKENES; ESTERS; ALDEHYDES
- Publication
Catalysts (2073-4344), 2023, Vol 13, Issue 1, p209
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal13010209