Efficient Synthesis of Octahydrophenanthrene Derivatives with Mild Cascade Reactions of Isochromenylium Tetrafluoroborates and Bifunctional Styrenes.
Efficient Synthesis of Octahydrophenanthrene Derivatives with Mild Cascade Reactions of Isochromenylium Tetrafluoroborates and Bifunctional Styrenes.
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DOI：
10.1021/acs.orglett.5b01532
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发表时间：
2015-06
期刊：
影响因子：
5.2
通讯作者：
Lei Mo;Linlin Wu;Shaozhong Wang;Z. Yao
中科院分区：
文献类型：
--
作者：
Lei Mo;Linlin Wu;Shaozhong Wang;Z. Yao
研究了一种高效的无催化剂级联反应，由空气稳定的异色烯四氟硼酸盐与含1，3-二酮结构的双官能苯乙烯反应，得到了相应的单一非对映体八氢菲衍生物（21个实例，产率高达86%）。通过[4 + 2]-环化和随后的分子内亲核加成的级联反应，提出了在反应中非对映选择性地生成三个新的C-C键。
A highly efficient catalyst-free cascade reaction of air-stable isochromenylium tetrafluoroborates and bifunctional styrenes containing a 1,3-diketone moiety has been developed, affording the corresponding single diastereomeric ocatahydrophenanthrene derivatives (21 examples, up to 86% yield). A cascade process of [4 + 2]-cyclization and subsequent intramolecular nucleophilic addition is proposed to generate the three new C-C bonds diastereoselectively in the reactions.