title: Ru-catalyzed asymmetric hydrogenation of 3-oxoglutaric acid derivatives via solvent-assisted pinpoint recognition of carbonyls in close chemical propinquity.
abstract: Upon comparison of hydrogenation rates of various β-ketocarboxylic acid derivatives, β-ketoamides were found to be hydrogenated slightly faster than β-ketoesters in EtOH in the presence of [RuCl(benzene)(S)-SunPhos]Cl at 70 °C with 20 bar of hydrogen. In THF these differences were so sharpened that β-ketoamides were hydrogenated even faster than in EtOH while the esters were extremely slow. Based on these findings, a series of 3-oxoglutaric acid derived with ester and amide moieties on the two ends were hydrogenated to 3-hydroxyl products with high enantioselectivities.
authors: School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.
authors: Wanfang
authors: W
authors: Li
authors: Xin
authors: X
authors: Ma
authors: Weizheng
authors: W
authors: Fan
authors: Xiaoming
authors: X
authors: Tao
authors: Xiaoming
authors: X
authors: Li
authors: Xiaomin
authors: X
authors: Xie
authors: Zhaoguo
authors: Z
authors: Zhang