کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
69202 | 48532 | 2006 | 4 صفحه PDF | دانلود رایگان |

A racemic mixture of methyl 3-cyclopropyl-2-methyl-3-oxopropanoate was hydrogenated over the tartaric acid-modified Raney nickel. Discrimination of the 2-methyl group during the reaction was high enough to perform the enantiomer differentiation, (2S)/(2R)-product = 16, and to cause an efficient dynamic kinetic resolution that resulted in one stereoisomer up to 93% of all the hydrogenation products. The diastereomer ratio was syn:anti = 97:3, and ee values of the respective diastereomers were 93% and 41%. However, the low reactivity of the substrate caused deactivation of the catalyst during the reaction and needed us to tune the reaction conditions to achieve both the high stereoselectivity and the high conversion. By introducing a small-scale reactor, 96% conversion was achieved with slight decrease in the enantiomer selectivity (=12).
A racemic mixture of methyl 3-cyclopropyl-2-methyl-3-oxopropanoate was hydrogenated over the tartaric acid-modified Raney nickel. Discrimination of the 2-methyl group during the reaction was high enough to perform the enantiomer differentiation, (2S)/(2R) = 16, and to cause an efficient dynamic kinetic resolution that resulted in one stereoisomer up to 93% of all the four hydrogenation products. Figure optionsDownload as PowerPoint slide
Journal: Journal of Molecular Catalysis A: Chemical - Volume 248, Issues 1–2, 3 April 2006, Pages 233–236