通过α-三氟甲基-α,β-不饱和羰基化合物与N-甲苯磺酰基-2-氨基丙二酸酯的串联反应合成2-氟-2-吡咯啉。
Synthesis of 2-fluoro-2-pyrrolines via tandem reaction of α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates.
作者信息
Yang Jieru, Zhou Xiaofan, Zeng Yu, Huang Chaoqian, Xiao Yuanjing, Zhang Junliang
机构信息
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P. R. China.
出版信息
Chem Commun (Camb). 2016 Apr 7;52(27):4922-5. doi: 10.1039/c6cc00831c. Epub 2016 Mar 15.
A simple base-mediated tandem SN2'/SNV reaction of the readily available α-trifluoromethyl-α,β-unsaturated carbonyl compounds with N-tosylated 2-aminomalonates was developed, which provide an efficient access to functionalized tetrasubstituted 2-fluoro-2-pyrrolines in good to excellent yields. In contrast, simple 1,2-nucleophilic adducts were produced when α-trifluoromethyl styrenes were used.
开发了一种简单的碱介导的串联SN2'/SNV反应，即容易获得的α-三氟甲基-α,β-不饱和羰基化合物与N-甲苯磺酰基-2-氨基丙二酸酯反应，该反应能以良好至优异的产率有效合成官能化的四取代2-氟-2-吡咯啉。相比之下，当使用α-三氟甲基苯乙烯时，则生成简单的1,2-亲核加合物。
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