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  • Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution.

Copper-catalyzed asymmetric hydrogenation of 2-substituted ketones via dynamic kinetic resolution.

Chemical science (2018-06-14)
Olga V Zatolochnaya, Sonia Rodríguez, Yongda Zhang, Kendricks S Lao, Sergei Tcyrulnikov, Guisheng Li, Xiao-Jun 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
PMID29896393
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.