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Sterically Hindered Chiral Ferrocenyl P,N,N-Ligands for Highly Diastereo-/Enantioselective Ir-Catalyzed Hydrogenation of α-Alkyl-β-ketoesters via Dynamic Kinetic Resolution
Organic Letters ( IF 4.9 ) Pub Date : 2016-10-21 00:00:00 , DOI: 10.1021/acs.orglett.6b02828
Chuan-Jin Hou 1, 2 , Xiang-Ping Hu 1
Organic Letters ( IF 4.9 ) Pub Date : 2016-10-21 00:00:00 , DOI: 10.1021/acs.orglett.6b02828
Chuan-Jin Hou 1, 2 , Xiang-Ping Hu 1
Affiliation
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A new class of sterically hindered chiral ferrocenyl P,N,N-ligands have been prepared through a two-step transformation from (Sc,Rp)-PPFNH2, in which a new (R)-stereogenic center at the pyridinylmethyl position was generated in high diastereoselectivity. With these newly developed P,N,N-ligands, Ir-catalyzed asymmetric hydrogenation of various α-alkyl-substituted β-aryl-β-ketoesters via dynamic kinetic resolution has been realized in high diastereo- and enantioselectivities for the first time, which led to a variety of optically active anti-β-hydroxyesters in up to 99% ee. The study indicated that the additional stereocenter at the pyridinylmethyl position of these ligands is crucial to realize this hydrogenation.
中文翻译:
通过动态动力学拆分对高非对映/对映选择性Ir催化的α-烷基-β-酮酸酯的手性受阻手性二茂铁基P,N,N-配体
通过从(S c,R p)-PPFNH 2的两步转化制备了新型的空间位阻性手性二茂铁基二茂铁基P,N,N-配体,其中在吡啶基甲基位置上有一个新的(R)-立体异构中心产生的非对映异构体选择性高。借助这些新开发的P,N,N配体,首次在高非对映体和对映体选择性下,通过动态动力学拆分实现了Ir催化的各种α-烷基取代的β-芳基-β-酮酸酯的不对称氢化,导致了多种光学活性的反-β-羟基酯含量高达99%ee。研究表明,这些配体的吡啶基甲基位置上的额外立体中心对于实现这种氢化作用至关重要。
更新日期:2016-10-21
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
通过动态动力学拆分对高非对映/对映选择性Ir催化的α-烷基-β-酮酸酯的手性受阻手性二茂铁基P,N,N-配体
通过从(S c,R p)-PPFNH 2的两步转化制备了新型的空间位阻性手性二茂铁基二茂铁基P,N,N-配体,其中在吡啶基甲基位置上有一个新的(R)-立体异构中心产生的非对映异构体选择性高。借助这些新开发的P,N,N配体,首次在高非对映体和对映体选择性下,通过动态动力学拆分实现了Ir催化的各种α-烷基取代的β-芳基-β-酮酸酯的不对称氢化,导致了多种光学活性的反-β-羟基酯含量高达99%ee。研究表明,这些配体的吡啶基甲基位置上的额外立体中心对于实现这种氢化作用至关重要。