Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs) via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: application for medicinally important N-heterocyclesElectronic supplementary information (ESI) available. See DOI: 10.1039/c6ra12965j

• Main Authors: Ramaraju, Panduga, Mir, Nisar A, Singh, Deepika, Kumar, Indresh
• Format: Journal Article
• Published: 22.06.2016
• ISSN: 2046-2069
• DOI: 10.1039/c6ra12965j

An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process. This transformation proceeds through proline-catalyzed direct Mannich reaction-cyclization of glutaraldehyde with in situ generated imines, followed by site-selective oxidation-reduction sequence under mild conditions. Chiral 1,2,5,6-THPs are obtained in good to high yields (up to 80%) and with the excellent enantioselectivity (up to 98 : 2 er). The usefulness of this operationally simple method is also shown to synthesize other medicinally important nitrogen-heterocycles. An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process.