Zheng Sheng-Cai, Wang Qian, Zhu Jieping
Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, École Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.
Angew Chem Int Ed Engl. 2019 Jan 28;58(5):1494-1498. doi: 10.1002/anie.201812654. Epub 2018 Dec 21.
We report herein the first examples of catalytic enantioselective synthesis of axially chiral 3-arylpyrroles. Reaction of α-isocyanoacetates with β-aryl-α,β-alkynic ketones in the presence of silver oxide and a phosphine ligand derived from Cinchona alkaloid occurred chemoselectively to afford enantioenriched 3-arylpyrroles in high yields with excellent enantiomeric excesses. The pyrrole ring was constructed de novo in this process.
我们在此报告轴向手性3-芳基吡咯催化对映选择性合成的首例。在氧化银和一种源自金鸡纳生物碱的膦配体存在下,α-异氰基乙酸酯与β-芳基-α,β-炔酮发生化学选择性反应,以高收率和优异的对映体过量得到对映体富集的3-芳基吡咯。在此过程中,吡咯环是从头构建的。