Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

Author:

Zhou Jiayu1,Ye Jianxun1,Zhang Yang1,Li Zhaodi1,Li Jingjing1,Liu Delong1ORCID,Zhang Wanbin12ORCID

Affiliation:

1. Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Pharmacy Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 People's Republic of China

2. Frontier Science Center for Transformative Molecules School of Chemistry and Chemical Engineering Shanghai Jiao Tong University 800 Dongchuan Road Shanghai 200240 People's Republic of China

Abstract

AbstractThe RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, (S)‐Orphenadrine and (S)‐Neobenodine. Deuterium labeling and control experiments revealed that the RuPHOX‐Ru‐catalyzed asymmetric hydrogenation is fully subject to hydrogenation with H2 as the sole hydrogen source.magnified image

Funder

National Natural Science Foundation of China

Shanghai Municipal Education Commission

Publisher

Wiley

Subject

General Chemistry

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