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首页> 外文期刊>Chemistry: A European journal >Polystyrene-supported diarylprolinol ethers as highly efficient organocatalysts for Michael-type reactions
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Polystyrene-supported diarylprolinol ethers as highly efficient organocatalysts for Michael-type reactions

机译：聚苯乙烯负载的二芳基脯氨醇醚作为迈克尔型反应的高效有机催化剂

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摘要

α,α-Diphenylprolinol methyl- and trimethylsilyl ethers anchored onto a polystyrene resin have been prepared by a copper-catalyzed azide-alkyne cycloadditions (CuAAC). The catalytic activity and enantioselectivity displayed by the O-trimethylsilyl derivative are comparable to those exhibited by the best known homogeneous catalysts for the addition of aldehydes to nitroolefins and of malonates or nitromethane to α,β-unsaturated aldehydes. The combination of the catalytic unit, the triazole linker, and the polymeric matrix provides unprecedented substrate selectivity, in favor of linear, short-chain aldehydes, when the organocatalyzed reaction proceeds by an enamine mechanism. High versatility is noted in reactions that proceed via an iminium ion intermediate. The catalytic behavior of polystyrene-supported α,α-diphenylprolinol methyl ether was also evaluated in asymmetric Michael addition reactions. As a general trend, the CuAAC immobilization of diarylprolinol ethers onto insoluble polystyrene resins offers important operational advantages, such as high catalytic activity, easy recovery from the reaction mixture by simple filtration, and the possibility of extended reuse.
机译：通过铜催化的叠氮化物-炔烃环加成反应（CuAAC）制备了锚定在聚苯乙烯树脂上的α，α-二苯基脯氨醇甲基和三甲基甲硅烷基醚。 O-三甲基甲硅烷基衍生物表现出的催化活性和对映选择性可与最著名的均相催化剂表现出的催化活性和对映选择性相比较，所述均相催化剂用于将醛添加至硝基烯烃，并将丙二酸酯或硝基甲烷添加至α，β-不饱和醛。当有机催化的反应通过烯胺机制进行时，催化单元，三唑连接基和聚合物基体的组合可提供空前的底物选择性，有利于线性短链醛。通过亚胺离子中间体进行的反应具有很高的通用性。还通过不对称迈克尔加成反应评价了聚苯乙烯负载的α，α-二苯基脯氨醇甲基醚的催化行为。通常，将二芳基脯氨醇醚固定在不溶性聚苯乙烯树脂上的CuAAC具有重要的操作优势，例如高催化活性，易于通过简单过滤从反应混合物中回收以及延长再利用的可能性。

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