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β-芳基亚烷基丙二酸酯的不对称氢化反应:引入酯基可显著提高反应效率。

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

作者信息

Zhao Qian-Kun, Wu Xiong, Li Lin-Ping, Yang Fan, Xie Jian-Hua, Zhou Qi-Lin

机构信息

State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

出版信息

Org Lett. 2021 Mar 5;23(5):1675-1680. doi: 10.1021/acs.orglett.1c00093. Epub 2021 Feb 18.

Abstract

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.

摘要

在此,我们报道了一种用于高效不对称氢化β-芳基亚烷基丙二酸酯的实用方法。使用位点特异性定制的手性螺环铱催化剂,一系列β-芳基亚烷基丙二酸酯被氢化,以提供对映选择性良好至优异(高达99% ee)且高周转数(高达19000)的手性丙二酸酯。结果表明,在α,β-不饱和羧酸酯中引入酯基显著提高了它们的不对称氢化反应效率。

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