Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines
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| Title: | Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines |
| Author: | Vidal Pereira, Xandro 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: | 2019 |
| Publisher: | American Chemical Society |
| Citation: | Vidal, X., Mascareñas, J., & Gulías, M. (2019). Palladium-Catalyzed, Enantioselective Formal Cycloaddition between Benzyltriflamides and Allenes: Straightforward Access to Enantioenriched Isoquinolines. J. Am. Chem. Soc., 141 (5), pp 1862–1866. doi: 10.1021/jacs.8b12636 |
| Abstract: | Benzyl and allyltriflamides can engage in Pd-catalyzed oxidative (4+2) annulations with allenes, to produce highly valuable tetrahydroisoquinoline or dihydropyridine skeletons. The reaction is especially efficient when carried out in the presence of designed N-protected amino acids as metal ligands. More importantly, using this type of chiral ligands, it is possible to perform desymmetrizing, annulative C–H activations of prochiral diarylmethylphenyl amides, and thus obtain the corresponding isoquinolines with high enantiomeric ratios |
| Publisher version: | https://doi.org/10.1021/jacs.8b12636 |
| URI: | http://hdl.handle.net/10347/18734 |
| DOI: | 10.1021/jacs.8b12636 |
| ISSN: | 0002-7863 |
| E-ISSN: | 1520-5126 |
| Rights: | © 2019 American Chemical Society. This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
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Except where otherwise noted, this item's license is described as © 2019 American Chemical Society. This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes