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Noyori asymmetric hydrogenation
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Noyori asymmetric hydrogenation : ウィキペディア英語版
Noyori asymmetric hydrogenation
In chemistry, the Noyori asymmetric hydrogenation of ketones is a chemical reaction for the enantioselective hydrogenation of ketone, aldehydes, and imines. This reaction exploits using chiral ruthenium catalysts introduced by Ryoji Noyori. He shared half of the Nobel Prize in Chemistry in 2001 with William S. Knowles for the study of the asymmetric hydrogenation.
BINAP-Ru catalyst is used for the asymmetric hydrogenation of functionalized ketones and BINAP/diamine-Ru catalyst is used for the asymmetric hydrogenation of simple ketones. These hydrogenations are used in the production of several drugs, such as the antibacterial levofloxin, the antibiotic carbapenem, and the antipsychotic agent BMS181100.
==History==
The stoichiometric asymmetric reduction of ketones has long been known, but a practical catalytic version was introduced by Noyori et al. While the BINAP-Ru dicarboxylate could only efficiently catalyze the hydrogenation of olefins, the BINAP-Ru dihalide could catalyze both the hydrogenation of olefins and the hydrogenation of functionalized C=O bond.

Even though the BINAP-Ru dihalide catalyst could reduce functionalized ketones, the hydrogenation of simple ketones has remained a challenge. In 1995, Noyori discovered that the RuCl2 (diphosphane)2 (diamine)2 complex can catalyze the hydrogenation of simple ketones. This system also had chemoselectivity on C=O bond over the C=C bond. The diastereoselectivity and the enantioselectivity〔 could be achieved at the same time using chiral BINAP ligand.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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