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Issue 19, 2018
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Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

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Abstract

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.

Graphical abstract: Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

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Publication details

The article was received on 26 Jan 2018, accepted on 19 Apr 2018 and first published on 23 Apr 2018


Article type: Edge Article
DOI: 10.1039/C8SC00434J
Citation: Chem. Sci., 2018,9, 4505-4510
  • Open access: Creative Commons BY license
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    Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution

    Olga V. Zatolochnaya, S. Rodríguez, Y. Zhang, K. S. Lao, S. Tcyrulnikov, G. Li, X. Wang, B. Qu, S. Biswas, H. P. R. Mangunuru, D. Rivalti, J. D. Sieber, J. Desrosiers, J. C. Leung, N. Grinberg, H. Lee, N. Haddad, N. K. Yee, J. J. Song, M. C. Kozlowski and C. H. Senanayake, Chem. Sci., 2018, 9, 4505
    DOI: 10.1039/C8SC00434J

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