Asymmetric Hydrogenation of α-Substituted Acrylic Acids Catalyzed by a Ruthenocenyl Phosphino-oxazoline–Ruthenium Complex

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• 作者：Jing Li ; Jiefeng Shen ; Chao Xia ; Yanzhao Wang ; Delong Liu ; Wanbin Zhang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：May 6, 2016
• 年：2016
• 卷：18
• 期：9
• 页码：2122-2125
• 全文大小：371K
• 年卷期：0
• ISSN：1523-7052

文摘

Asymmetric hydrogenation of various α-substituted acrylic acids was carried out using RuPHOX–Ru as a chiral catalyst under 5 bar H₂, affording the corresponding chiral α-substituted propanic acids in up to 99% yield and 99.9% ee. The reaction could be performed on a gram-scale with a relatively low catalyst loading (up to 5000 S/C), and the resulting product (97%, 99.3% ee) can be used as a key intermediate to construct bioactive chiral molecules. The asymmetric protocol was successfully applied to an asymmetric synthesis of dihydroartemisinic acid, a key intermediate required for the industrial synthesis of the antimalarial drug artemisinin.