Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition
Z-Selective Synthesis of Vinyl Boronates through Fe-Catalyzed Alkyl Radical Addition
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DOI：
10.1021/acs.orglett.8b03772
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发表时间：
2019-01-18
期刊：
影响因子：
5.2
通讯作者：
Hu, Xile
中科院分区：
文献类型：
--
作者：
Barzano, Guido;Cheseaux, Alexis;Hu, Xile
硼酸乙烯酯的Z-选择性合成具有挑战性。本工作描述了Fe催化的由相应的烷基卤化物形成的烷基自由基与乙炔基乙炔基硼酸频哪醇酯的加成，从而以高立体选择性产生Z-乙烯基硼酸酯。该方法对叔烷基碘和仲烷基碘效果最好。Z-乙烯基硼酸酯产物通过硼酸酯基团的转化容易地转化为其它Z-烯烃。该方法应用于5-HT 2c受体激动剂的正式全合成。
Z-Selective synthesis of vinyl boronates is challenging. This work describes Fe-catalyzed addition of alkyl radicals, formed by the corresponding alkyl halides, to ethynyl ethynylboronic acid pinacol ester that gives rise to Z-vinyl boronates in high stereoselectivity. The method works best for tertiary and secondary alkyl iodides. The Z-vinyl boronate products are easily converted to other Z-alkenes by transformation of the boronate group. The method is applied for the formal total synthesis of a 5-HT2c receptor agonist.