Efficient Access to Chiral Benzhydrols via Asymmetric Transfer Hydrogenation of Unsymmetrical Benzophenones with Bifunctional Oxo-Tethered Ruthenium Catalysts

Taichiro Touge*, Hideki Nara, Mitsuhiko Fujiwhara, Yoshihito Kayaki* and Takao Ikariya

*Takasago International Corporation, Kanagawa 254-0073; Tokyo Institute of Technology, 2-12-1-E4-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan, Email: taichiro_tougetakasago.com, ykayakio.cc.titech.ac.jp

T. Touge, H. Nara, M. Fujiwhara, Y. Kayaki, T. Ikariya, J. Am. Chem. Soc., 2016, 138, 10084-10087.

DOI: 10.1021/jacs.6b05738

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Abstract

An asymmetric transfer hydrogenation of diaryl ketones is promoted by bifunctional Ru complexes with an etherial linkage between 1,2-diphenylethylenediamine (DPEN) and η⁶-arene ligands. An effective discrimination of substituents on the aryl group enables a smooth reduction in a 5:2 mixture of formic acid and triethylamine with a high level of enantioselectivity.

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Key Words

reduction of ketones, formic acid

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ID: J48-Y2016