Highly Enantioselective Sequential Hydrogenation of Ethyl 2-Oxo-4-arylbut-3-enoate to Ethyl 2-Hydroxy-4-arylbutyrate
Authors:
- 22 August 2008
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 73 (18) , 7209-7212
Abstract
The hydrogenation of (E)-ethyl 2-oxo-4-arylbut-3-enoate with [NH2Me2]+[{RuCl [(S)-SunPhos]}2(μ-Cl3)] gave ethyl 2-hydroxy-4-arylbutyrate with 94−96% ee. Further investigation has proved that the hydrogenation proceeded via a sequential hydrogenation of C═O and C═C bonds, which is sensitive to the reaction temperature. Hydrolysis of ethyl 2-hydroxy-4-phenylbutyrate (ee 93%) provided the 2-hydroxy-4-phenylbutyric acid with 81% yield at 99% ee after a single recrystallization from 1, 2-dichloroethylene.Keywords
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