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Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones <i>via</i> dynamic kinetic resolution

Olga V. Zatolochnaya,Sonia Rodrı́guez,Yongda Zhang,Kendricks S. Lao,Sergei Tcyrulnikov,Guisheng Li,Xiaojun Wang,Bo Qu,Soumik Biswas,Hari P. R. Mangunuru,Daniel Rivalti,Joshua D. Sieber,Jean‐Nicolas Desrosiers,Joyce C. Leung,Nelu Grinberg,Heewon Lee,Nizar Haddad,Nathan K. Yee,Jinhua J. Song,Marisa C. Kozlowski,Chris H. Senanayake

Kinetic resolution

Stereocenter

Catalysis

2018

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.

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“Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones <i>via</i> dynamic kinetic resolution” is a paper by Olga V. Zatolochnaya Sonia Rodrı́guez Yongda Zhang Kendricks S. Lao Sergei Tcyrulnikov Guisheng Li Xiaojun Wang Bo Qu Soumik Biswas Hari P. R. Mangunuru Daniel Rivalti Joshua D. Sieber Jean‐Nicolas Desrosiers Joyce C. Leung Nelu Grinberg Heewon Lee Nizar Haddad Nathan K. Yee Jinhua J. Song Marisa C. Kozlowski Chris H. Senanayake published in 2018. It has an Open Access status of “gold”. You can read and download a PDF Full Text of this paper here.