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

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journal contribution
posted on 2021-09-08, 15:37 authored by Zhizhao Wang, Guoren Yue, Xiangdong Ji, Hai Song, Penji Yan, Jixing Zhao, Xin Jia
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.

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