Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines
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| Title: | Kinetic Resolution of Allyltriflamides through a Pd-Catalyzed C–H Functionalization with Allenes: Asymmetric Assembly of Tetrahydropyridines |
| Author: | González González, José Manuel Cendón Mariño, Borja Mascareñas Cid, José Luis Gulías Costa, Moisés |
| Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Date of Issue: | 2021 |
| Publisher: | American Chemical Society |
| Citation: | J. Am. Chem. Soc. 2021, 143, 10, 3747–3752 |
| Abstract: | Enantioenriched, six-membered azacycles are essential structural motifs in many products of pharmaceutical or agrochemical interest. Here we report a simple and practical method for enantioselective assembly of tetrahydropyridines, which is paired to a kinetic resolution of α-branched allyltriflamides. The reaction consists of a formal (4+2) cycloaddition between the allylamine derivatives and allenes and is initiated by a palladium(II)-catalyzed C–H activation process. Both the chiral allylamide precursors and the tetrahydropyridine adducts were successfully obtained in high yields, with excellent enantioselectivity (up to 99% ee) and selectivity values of up to 127 |
| Publisher version: | https://doi.org/10.1021/jacs.1c01929 |
| URI: | http://hdl.handle.net/10347/24850 |
| DOI: | 10.1021/jacs.1c01929 |
| ISSN: | 0002-7863 |
| E-ISSN: | 1520-5126 |
| Rights: | © 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/) |
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Except where otherwise noted, this item's license is described as © 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)