Preparation of Optically Active 2-(Trifluoromethyl)alkan-1-ols by Catalytic Asymmetric Hydrogenation

Katsuhiko ISEKI; Yoshichika KUROKI; Takabumi NAGAI; Yoshiro KOBAYASHI

doi:10.1248/cpb.44.477

Katsuhiko ISEKI, Yoshichika KUROKI, Takabumi NAGAI, Yoshiro KOBAYASHI

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Keywords: asymmetric hydrogenation, asymmetric synthesis, chiral fluorinated compound, 2-(trifluoromethyl)alkan-1-ol, 2, 2'-bis(diphenylphosphino)-1, 1'-binaphythyl

JOURNAL FREE ACCESS

1996 Volume 44 Issue 3 Pages 477-480

DOI https://doi.org/10.1248/cpb.44.477

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Abstract

The hydrogenation of (E)-2-(trifluoromethyl)alk-2-en-1-ols catalyzed by Ru-2, 2'-bis(diphynylphosphino)-1, 1'-binaphthyl (Ru-BINAP) and Rh-BINAP was carried out with good enantiomeric excess (71-83% ee). Ru-BINAP-catalyzed hydrogenation converted 2-(trifluoromethyl)acrylic acid to the corresponding saturated acid whose esterification and reduction provided optically active 2-(trifluoromethyl)propan-1-ol in 80% ee.

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