Tandem Michael Addition–Cyclization of Nitroalkenes with 1,3-Dicarbonyl Compounds Accompanied by Removal of Nitro Group

A tandem Michael addition–cyclization of nitroalkenes with 1,3-dicarbonyl compounds was developed using phase transfer catalyst (PTC), allowing for the synthesis of polysubstituted-[4,5]-dihydrofuran in high yields. A wide range of substrates were demonstrated by this one-step process. Meanwhile, nitro group was substituted to form corresponding nitrite ion detected in the aqueous phase providing a reasonable pathway for denitrating poisonous and explosive nitro-containing compounds. The proposed mechanism was also supported by our DFT calculations.本研究开发了以相转移催化剂（PTC）催化的硝基烯烃与1,3-二羰基化合物的迈克尔加成-环化串联反应，可高产率合成多取代-[4,5]-二氢呋喃。该一步法工艺可兼容多种底物。与此同时，反应中的硝基被取代为亚硝酸根离子并可在水相中被检测到，该过程为脱除有毒且易爆的含硝基化合物提供了可行路径。我们通过密度泛函理论（Density Functional Theory, DFT）计算验证了所提出的反应机理。