Practical synthesis of enantiopure benzylamines by catalytic hydrogenation or transfer hydrogenation reactions in isopropanol using a Ru-pybox catalyst†,Organic Chemistry Frontiers

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Practical synthesis of enantiopure benzylamines by catalytic hydrogenation or transfer hydrogenation reactions in isopropanol using a Ru-pybox catalyst†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-12-01 00:00:00 , DOI: 10.1039/c7qo00908a
E. de Julián _{1,

2,

3,

4,

5} , E. Menéndez-Pedregal _{1,

2,

3,

4,

5} , M. Claros _{1,

2,

3,

4,

5} , M. Vaquero _{6,

7,

8,

9} , J. Díez _{1,

2,

3,

4,

5} , E. Lastra _{1,

2,

3,

4,

5} , P. Gamasa _{1,

2,

3,

4,

5} , A. Pizzano _{6,

7,

8,

9}

Affiliation

The screening of a family of complexes of the formula [RuCl₂(R-pybox)(L)] (R-pybox = Ph-, ⁱPr- or indane-pybox; L = monodentate P, N or C ligand) in the enantioselective hydrogenation of N-aryl imines indicates a strong influence of the R-pybox substituents and the L ligand in the process. A comparison indicates that the best results are obtained with the complex [RuCl₂(Ph-pybox)(PPh(OMe)₂)] which provided values of 99% ee for the reduction of several imines derived from aryl alkyl ketones. It is worth noting that this complex is capable of reducing the mentioned imines under transfer hydrogenation conditions using isopropanol as a hydrogen donor with equally high enantioselectivities.

中文翻译：

使用Ru-pybox催化剂在异丙醇中通过催化氢化或转移氢化反应实际合成对映体纯的苄胺†

在分子筛中筛选式[RuCl ₂（R-pybox）（L）]（R-pybox = Ph-，ⁱ Pr-或茚满-pybox; L =单齿P，N或C配体）的配合物家族N-芳基亚胺的对映选择性氢化表明，R-pybox取代基和L配体在此过程中具有强大的影响力。比较表明，使用配合物[RuCl ₂（Ph-pybox）（PPh（OMe）₂）]可获得最佳结果，该配合物可提供99％ee的值，可还原衍生自芳基烷基酮的几种亚胺。值得注意的是，该络合物在转移氢化条件下使用异丙醇作为具有相同高对映选择性的氢供体，能够还原所述亚胺。

更新日期：2017-12-01

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