A Nickel‐Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes,Advanced Synthesis & Catalysis

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A Nickel‐Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-09-28 , DOI: 10.1002/adsc.202000875
Mikkel Buendia ₁ , Søren Kegnæs ₁ , Soren Kramer ₁

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We report a polystyrene‐incorporated chiral nickel(II)‐bisdiamine complex, which is accessible on gram‐scale. This metal complex functions as a heterogeneous catalyst for the enantioselective Michael addition between malonates and aliphatic nitroalkenes, and it provides yields and enantioselectivities on par with homogeneous catalysts. Good functional group tolerance is reported for this reaction. Upon recycling, the catalyst achieves significantly higher TONs than previously reported. We demonstrate scalability to multigram‐scale, compatibility with continuous flow production (4.43 gram), and application to the synthesis of the blockbuster drug Pregabalin. Finally, a new tandem reaction is disclosed.

中文翻译：

镍-双二胺多孔有机聚合物作为脂肪族硝基烯烃不对称迈克尔加成的均相手性催化剂

我们报道了一种聚苯乙烯结合的手性镍（II）-双二胺络合物，其克级可访问。该金属络合物充当丙二酸酯和脂肪族硝基烯烃之间对映选择性迈克尔加成反应的非均相催化剂，与均相催化剂相比，它提供了收率和对映选择性。据报道该反应具有良好的官能团耐受性。再循环后，该催化剂的TONs明显高于以前报道的水平。我们展示了可扩展至数克级的规模，与连续生产量（4.43克）的相容性以及在重磅炸药普瑞巴林的合成中的应用。最后，公开了新的串联反应。

更新日期：2020-09-28

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