Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters
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| Title: | Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters |
| Author: | Arribas Domingo, Andrés Calvelo Souto, Martín Fernández Fernández, David Rodrigues, Catarina A. B. Mascareñas Cid, José Luis López García, Fernando |
| Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
| Subject: | C-H activation | Enantioselective | Heterocycles | Hydrocarbonation | Iridium | |
| Date of Issue: | 2021 |
| Publisher: | Wiley |
| Citation: | Arribas, A., Calvelo, M., Fernández, D.F., Rodrigues, C.A.B., Mascareñas, J.L. and López, F. (2021), Highly Enantioselective Iridium(I)-Catalyzed Hydrocarbonation of Alkenes: A Versatile Approach to Heterocyclic Systems Bearing Quaternary Stereocenters. Angew. Chem. Int. Ed.. https://doi.org/10.1002/anie.202105776 |
| Abstract: | We report a versatile, highly enantioselective intramolecular hydrocarbonation reaction that provides a direct access to heteropolycyclic systems bearing chiral quaternary carbon stereocenters. The method, which relies on an iridium(I)/bisphosphine chiral catalyst, is particularly efficient for the synthesis of five-, six- and seven-membered fused indole and pyrrole products, bearing one and two stereocenters, with enantiomeric excesses of up to >99 %. DFT computational studies allowed to obtain a detailed mechanistic profile and identify a cluster of weak non-covalent interactions as key factors to control the enantioselectivity |
| Publisher version: | https://doi.org/10.1002/anie.202105776 |
| URI: | http://hdl.handle.net/10347/26623 |
| DOI: | 10.1002/anie.202105776 |
| ISSN: | 1433-7851 |
| E-ISSN: | 1521-3773 |
| Rights: | © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
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Except where otherwise noted, this item's license is described as © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made