Practical synthesis of (S)-1-(3-trifluoromethylphenyl)ethanol via ruthenium(II)-catalyzed asymmetric transfer hydrogenation

Citation
M. Miyagi et al., Practical synthesis of (S)-1-(3-trifluoromethylphenyl)ethanol via ruthenium(II)-catalyzed asymmetric transfer hydrogenation, ORG PROC R, 4(5), 2000, pp. 346-348
Citations number
20
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC PROCESS RESEARCH & DEVELOPMENT
ISSN journal
10836160 → ACNP
Volume
4
Issue
5
Year of publication
2000
Pages
346 - 348
Database
ISI
SICI code
1083-6160(200009/10)4:5<346:PSO(VR>2.0.ZU;2-5
Abstract
(S)-1-(3-Trifluoromethylphenyl)ethanol which is useful as an agrochemical i ntermediate was prepared from the corresponding acetophenone by asymmetric transfer hydrogenation. Removal of acetone raised the yield and maintained the optical purity when i-PrOH was used as the hydrogen source; however, th is operation was not practical at industrial scale. Then formic acid was ex amined as the hydrogen source, and dramatic acceleration of the reaction ra te was achieved by optimization of the reaction conditions to establish asy mmetric transfer hydrogenation at industrial scale.