Asymmetric Hydrogenation of β-Aryl Alkylidene Malonate Esters: Installing an Ester Group Significantly Increases the Efficiency,Organic Letters

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Asymmetric Hydrogenation of β-Aryl Alkylidene Malonate Esters: Installing an Ester Group Significantly Increases the Efficiency
Organic Letters ( IF 4.9 ) Pub Date : 2021-02-18 , DOI: 10.1021/acs.orglett.1c00093
Qian-Kun Zhao ₁ , Xiong Wu ₁ , Lin-Ping Li ₁ , Fan Yang ₁ , Jian-Hua Xie ₁ , Qi-Lin Zhou ₁

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Herein, we report a practical method for efficient asymmetric hydrogenation of β-aryl alkylidene malonates. With a site-specifically tailored chiral spiro iridium catalyst, a series of β-aryl alkylidene malonate esters were hydrogenated to afford chiral malonate esters with good to excellent enantioselectivities (up to 99% ee) and high turnover numbers (up to 19000). The results showed that installing an ester group in α,β-unsaturated carboxylic esters significantly increased the efficiency of their asymmetric hydrogenation reactions.

中文翻译：

β-芳基亚烷基丙二酸酯的不对称加氢：安装酯基显着提高了效率

在此，我们报告了一种有效的不对称氢化β-芳基亚烷基丙二酸酯的实用方法。使用针对特定位置的手性螺铱铱催化剂，一系列β-芳基亚烷基丙二酸酯被氢化，得到手性丙二酸酯，具有良好的对映体选择性（高达99％ee）和高周转率（高达19000）。结果表明，在α，β-不饱和羧酸酯中安装酯基显着提高了其不对称氢化反应的效率。

更新日期：2021-03-05

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