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

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.

SUBMITTER: Zatolochnaya OV

PROVIDER: S-EPMC5958347 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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

Zatolochnaya Olga V OV Rodríguez Sonia S Zhang Yongda Y Lao Kendricks S KS Tcyrulnikov Sergei S Li Guisheng G Wang Xiao-Jun XJ Qu Bo B Biswas Soumik S Mangunuru Hari P R HPR Rivalti Daniel D Sieber Joshua D JD Desrosiers Jean-Nicolas JN Leung Joyce C JC Grinberg Nelu N Lee Heewon H Haddad Nizar N Yee Nathan K NK Song Jinhua J JJ Kozlowski Marisa C MC Senanayake Chris H CH

Chemical science 20180423 19

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 dime ...[more]

PMID: 29896393

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