Highly Enantioselective Rhodium-Catalyzed Hydrogenation of 2-(2-Methoxy-2-oxoethyl)acrylic Acid − A Convenient Access of Enantiomerically Pure Isoprenoid Building Blocks

Autor: Ostermeier, Markus, Brunner, Bernhard, Korff, Christian, Helmchen, Günter
Zdroj: European Journal of Organic Chemistry; September 2003, Vol. 2003 Issue: 17 p3453-3459, 7p
Abstrakt: Asymmetric catalytic hydrogenation of 2-(2-methoxy-2-oxoethyl)acrylic acid (5) to give (2S)-4-methoxy-2-methyl-4-oxobutanoic acid [(S)-6] was studied. An enantiomeric excess of 99.7% ee was achieved with a catalyst formed in situ from [Rh(COD)2]BF4 and the chiral phosphite L2 in 1,2-dichloroethane as solvent. In addition, enzyme-catalyzed semi-saponification of dimethyl 2-methylsuccinate was investigated. Mono ester (S)-6 was transformed into a few compounds which can serve as C5-building blocks in natural product syntheses. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Databáze: Supplemental Index