Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives†,Organic Chemistry Frontiers

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Ruthenium-catalyzed dynamic kinetic asymmetric transfer hydrogenation: stereoselective access to syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-02-28 00:00:00 , DOI: 10.1039/c7qo01142c
Long-Sheng Zheng _{1,

2,

3,

4,

5} , Phannarath Phansavath _{1,

2,

3,

4,

5} , Virginie Ratovelomanana-Vidal _{1,

2,

3,

4,

5}

Affiliation

An efficient, stereoselective route to 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives through an asymmetric transfer hydrogenation of ring-substituted β-amino ketones via dynamic kinetic resolution has been developed. The reaction proceeded under mild conditions in the presence of RuCl[(S,S)-TsDPEN](benzene) and HCO₂H/Et₃N (5 : 2) as the hydrogen source, delivering in good yields a variety of syn 2-(1,2,3,4-tetrahydro-1-isoquinolyl)ethanol derivatives with excellent enantioselectivities (up to 99% ee) and diastereomeric ratios up to 71 : 29 dr.

中文翻译：

钌催化的动态动力学不对称转移氢化反应：立体选择性地获得合成的2-（1,2,3,4-四氢-1-异喹啉基）乙醇衍生物†

已经开发了通过动态动力学拆分通过环取代的β-氨基酮的不对称转移氢化而形成2-（1,2,3,4-四氢-1-异喹啉基）乙醇衍生物的有效的立体选择性途径。反应在温和的条件下，在RuCl [（S，S）-TsDPEN]（苯）和HCO ₂ H / Et ₃ N（5：2）作为氢源的条件下进行，以高产率提供了多种syn 2 -（1,2,3,4-四氢-1-异喹啉基）乙醇衍生物，具有出色的对映选择性（高达99％ee）和非对映体比率高达71:29 dr。

更新日期：2018-02-28

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