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Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones via dynamic kinetic resolution, simultaneously creating two contiguous s...
| Autores principales: | , , , , , , , , , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Royal Society of Chemistry
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5958347/ https://www.ncbi.nlm.nih.gov/pubmed/29896393 http://dx.doi.org/10.1039/c8sc00434j |
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| author | Zatolochnaya, Olga V. Rodríguez, Sonia Zhang, Yongda Lao, Kendricks S. Tcyrulnikov, Sergei Li, Guisheng Wang, Xiao-Jun Qu, Bo Biswas, Soumik Mangunuru, Hari P. R. Rivalti, Daniel Sieber, Joshua D. Desrosiers, Jean-Nicolas Leung, Joyce C. Grinberg, Nelu Lee, Heewon Haddad, Nizar Yee, Nathan K. Song, Jinhua J. Kozlowski, Marisa C. Senanayake, Chris H. |
| author_facet | Zatolochnaya, Olga V. Rodríguez, Sonia Zhang, Yongda Lao, Kendricks S. Tcyrulnikov, Sergei Li, Guisheng Wang, Xiao-Jun Qu, Bo Biswas, Soumik Mangunuru, Hari P. R. Rivalti, Daniel Sieber, Joshua D. Desrosiers, Jean-Nicolas Leung, Joyce C. Grinberg, Nelu Lee, Heewon Haddad, Nizar Yee, Nathan K. Song, Jinhua J. Kozlowski, Marisa C. Senanayake, Chris H. |
| author_sort | Zatolochnaya, Olga V. |
| collection | PubMed |
| description | A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones via dynamic kinetic resolution, simultaneously creating two contiguous stereogenic centers with up to >99 : 1 dr and 98 : 2 er. The ligand-Cu complexes were isolated and characterized by single crystal X-ray, and DFT calculations revealed a novel heteroligated dimeric copper hydride transition state. |
| format | Online Article Text |
| id | pubmed-5958347 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | Royal Society of Chemistry |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-59583472018-06-12 Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution Zatolochnaya, Olga V. Rodríguez, Sonia Zhang, Yongda Lao, Kendricks S. Tcyrulnikov, Sergei Li, Guisheng Wang, Xiao-Jun Qu, Bo Biswas, Soumik Mangunuru, Hari P. R. Rivalti, Daniel Sieber, Joshua D. Desrosiers, Jean-Nicolas Leung, Joyce C. Grinberg, Nelu Lee, Heewon Haddad, Nizar Yee, Nathan K. Song, Jinhua J. Kozlowski, Marisa C. Senanayake, Chris H. Chem Sci Chemistry A new class of tunable heterophosphole dimeric ligands have been designed and synthesized. These ligands have enabled the first examples of Cu-catalyzed hydrogenation of 2-substituted-1-tetralones and related heteroaryl ketones via dynamic kinetic resolution, simultaneously creating two contiguous stereogenic centers with up to >99 : 1 dr and 98 : 2 er. The ligand-Cu complexes were isolated and characterized by single crystal X-ray, and DFT calculations revealed a novel heteroligated dimeric copper hydride transition state. Royal Society of Chemistry 2018-04-23 /pmc/articles/PMC5958347/ /pubmed/29896393 http://dx.doi.org/10.1039/c8sc00434j Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
| spellingShingle | Chemistry Zatolochnaya, Olga V. Rodríguez, Sonia Zhang, Yongda Lao, Kendricks S. Tcyrulnikov, Sergei Li, Guisheng Wang, Xiao-Jun Qu, Bo Biswas, Soumik Mangunuru, Hari P. R. Rivalti, Daniel Sieber, Joshua D. Desrosiers, Jean-Nicolas Leung, Joyce C. Grinberg, Nelu Lee, Heewon Haddad, Nizar Yee, Nathan K. Song, Jinhua J. Kozlowski, Marisa C. Senanayake, Chris H. Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution |
| title | Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
|
| title_full | Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
|
| title_fullStr | Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
|
| title_full_unstemmed | Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
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| title_short | Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution
|
| title_sort | copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution |
| topic | Chemistry |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5958347/ https://www.ncbi.nlm.nih.gov/pubmed/29896393 http://dx.doi.org/10.1039/c8sc00434j |
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