Chiral Functionalization of a Zirconium Metal–Organic Framework (DUT-67) as a Heterogeneous Catalyst in Asymmetric Michael Addition Reaction,Inorganic Chemistry

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Chiral Functionalization of a Zirconium Metal–Organic Framework (DUT-67) as a Heterogeneous Catalyst in Asymmetric Michael Addition Reaction
Inorganic Chemistry ( IF 4.3 ) Pub Date : 2018-01-24 00:00:00 , DOI: 10.1021/acs.inorgchem.7b02854
Khoa D. Nguyen ₁ , Christel Kutzscher ₁ , Franziska Drache ₁ , Irena Senkovska ₁ , Stefan Kaskel ₁

Affiliation

DUT-67, an 8-connected zirconium and 2,5-thiophenedicarboxylate-based metal–organic framework (MOF), was postsynthetically functionalized by l-proline via solvent-assisted linker incorporation to obtain a chiral base catalyst. The parent monocarboxylate could be almost completely exchanged by l-proline after 5 days of treatment. The resulting chiral DUT-67 was demonstrated to be a promising heterogeneous catalyst for the asymmetric Michael addition of cyclohexanone to trans-β-nitrostyrene with excellent yield (up to 96%) and enantioselectivity comparable to that of l-proline in homogeneous reaction (ee of approximately 38%). The Zr-MOF could be reused at least five times without substantial degradation in the crystallinity or catalytic activity. No leaching of catalytically active species into the liquid phase was detected over five cycles.

中文翻译：

锆金属-有机骨架（DUT-67）在不对称迈克尔加成反应中作为多相催化剂的手性官能化

DUT-67是一种8-连接的锆和2,5-噻吩二羧酸盐基的金属有机骨架（MOF），通过溶剂辅助的连接基团被l-脯氨酸合成后官能化，从而获得手性碱催化剂。处理5天后，母体单羧酸盐几乎可以完全被1-脯氨酸交换。所得手性DUT-67被证明是一种有前途的多相催化剂，可将环己酮不对称迈克尔加成到反式-β-硝基苯乙烯上，具有极佳的收率（高达96％），对映选择性可与1相比。-脯氨酸在均相反应中（ee约为38％）。Zr-MOF可以重复使用至少五次，而不会显着降低结晶度或催化活性。在五个循环中未检测到催化活性物质向液相中的浸出。

更新日期：2018-01-24

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