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
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-select...
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| Format | Journal Article |
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22.06.2016
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| Abstract | 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. |
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| AbstractList | 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. |
| Author | Singh, Deepika Kumar, Indresh Ramaraju, Panduga Mir, Nisar A |
| AuthorAffiliation | Department of Chemistry Birla Institute of Technology and Science IIIM-CSIR Lab Instrumentation Division |
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| Author_xml | – sequence: 1 givenname: Panduga surname: Ramaraju fullname: Ramaraju, Panduga – sequence: 2 givenname: Nisar A surname: Mir fullname: Mir, Nisar A – sequence: 3 givenname: Deepika surname: Singh fullname: Singh, Deepika – sequence: 4 givenname: Indresh surname: Kumar fullname: Kumar, Indresh |
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| References_xml | – issn: 1999 publication-title: Iminosugars as Glycosidase Inhibitors: Nojirimycin & Beyond doi: Stütz – issn: 2006 publication-title: Domino Reactions in Organic Synthesis doi: Tietze Brasche Gericke – issn: 1987 publication-title: Hetero Diels-Alder Methodology in Organic Synthesis doi: Boger Weinreb – issn: 2005 publication-title: Asymmetric Organocatalysis doi: Berkessel Gröger – issn: 2001 issue: vol. 55 publication-title: The Alkaloids doi: Michael – issn: 2005 publication-title: Multicomponent Reactions doi: Zhu Bienayme |
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| Title | 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 |
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