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Rh/Wudaphos 催化的对甲苯亚磺酸钠的不对称氢化:一种获得手性 α-芳基乙基砜酸的方法。

Rh/Wudaphos-Catalyzed Asymmetric Hydrogenation of Sodium α-Arylethenylsulfonates: A Method To Access Chiral α-Arylethylsulfonic Acids.

机构信息

College of Chemistry and Molecular Sciences, Wuhan University , Wuhan, Hubei 430072, P. R. China.

Department of Chemistry, South University of Science and Technology of China , Shenzhen, Guangdong 518055, P. R. China.

出版信息

Org Lett. 2017 May 19;19(10):2678-2681. doi: 10.1021/acs.orglett.7b01021. Epub 2017 May 9.

Abstract

A highly enantioselective hydrogenation of various sodium α-arylethenylsulfonates catalyzed by Rh/chiral ferrocenyl bisphosphorus ligand (Wudaphos) was successfully developed to construct a series of chiral α-arylethylsulfonic acids in the presence of CFSOH with full conversion and good to excellent enantioselectivity (>99% conversion, up to 96% ee) under mild reaction conditions for the first time. Moreover, the control experiment results showed that the non-covalent ion pair interaction between the α-arylethenylsulfonic acid and the Wudaphos ligand plays an important role in this asymmetric hydrogenation system.

摘要

手性二茂铁膦配体(Wudaphos)促进的铑催化各种芳基烯基砜酸钠的高对映选择性氢化反应,在 CFSOH 存在下,在温和的反应条件下,首次成功构建了一系列手性α-芳基乙基砜,转化率高,对映选择性好(>99%转化率,高达 96%ee)。此外,控制实验结果表明,α-芳基烯基砜与 Wudaphos 配体之间的非共价离子对相互作用在这个不对称氢化体系中起着重要作用。

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