Optimization of asymmetric hydrogenation of 3-phenyl-3-butenoic acid catalyzed by rhodium(I)-4,5-bis[(diphenylphosphino)methyl]-2,2-dimethyldioxolane (DIOP)☆☆☆

Add time:08/31/2019    Source:sciencedirect.com

Enantioselective, homogeneous hydrogenation of 3-phenyl-3-butenoic acid (1) has extensively been examined in the presence of the rhodium(I)/4,5-bis[(diphenylphosphino)methyl]-2,2-dimethyldioxolane (DIOP) catalyst systems. Optimization of the reaction conditions was undertaken mainly by controlling effects of added tertiary amines as well as solvent polarities on the enantio-selectivity of the product. The best asymmetric yield (85.1% e.e.) was attained when the hydrogenation was carried out in the presence of triethylamine (5 mol%) in 75% aqueous methanol using a neutral rhodium-DIOP catalyst.

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