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钌催化的通过 DKR 不对称转移氢化高对映选择性合成 -3-奎宁环醇。

Ruthenium-Catalyzed Highly Enantioselective Synthesis of -3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation.

机构信息

School of Biology and biological Engineering, South China University of Technology, Guangzhou 510640, P.R. China.

State Key Laboratory of Anti-Infective Drug Development, Sunshine Lake Pharma Co., Ltd., Dongguan 523871, P.R. China.

出版信息

Org Lett. 2020 Jun 5;22(11):4322-4326. doi: 10.1021/acs.orglett.0c01361. Epub 2020 May 14.

Abstract

A method for the enantioselective synthesis of -3-quinuclidinols by Ru-catalyzed asymmetric transfer hydrogenation via dynamic kinetic resolution is described. The reaction proceeded under mild conditions using ammonium formate as the hydrogen donor, affording the products in high yields (up to 99%) with excellent diastereoselectivity (up to 99:1 dr) and enantioselectivity (95-99% ee). This protocol was applicable to gram-scale preparation with perfect enantioselectivity through simple recrystallization.

摘要

描述了一种通过 Ru 催化的不对称转移氢化通过动态动力学拆分对 -3-奎宁醇进行对映选择性合成的方法。该反应在温和条件下进行,使用甲酸铵作为氢供体,以高收率(高达 99%)、极好的非对映选择性(高达 99:1 dr)和对映选择性(95-99%ee)得到产物。该方案通过简单的重结晶适用于克级制备,具有完美的对映选择性。

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