Organocatalytic Cloke-Wilson Rearrangement: Carbocation-Initiated Tandem Ring Opening/Cyclization of Cyclopropanes under Neutral Conditions.
Organocatalytic Cloke-Wilson Rearrangement: Carbocation-Initiated Tandem Ring Opening/Cyclization of Cyclopropanes under Neutral Conditions.
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DOI：
10.1021/acs.joc.2c02415
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发表时间：
2023-01
期刊：
影响因子：
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通讯作者：
Guisheng Zhang;Liming Chen;Zhaokang Hu;Zhiguo Zhang;Jingjing Bi;Mengjuan Li;Xing-Song Zhang
中科院分区：
文献类型：
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作者：
Guisheng Zhang;Liming Chen;Zhaokang Hu;Zhiguo Zhang;Jingjing Bi;Mengjuan Li;Xing-Song Zhang
我们报道了一种无金属、无酸、无碱的2-（溴乙基）萘（2- bmn）促进链双活化环丙烷的有机催化clok - wilson重排，通过碳正离子引发的串联分子内开环/循环过程构建2,3-二氢呋喃。该策略特别适用于复杂分子中呋喃单元的构建，解决了传统金属基方法合成含二氢呋喃药物中重金属残留的问题。因此，它在合成化学和药物化学中具有潜在的研究价值。
We report a metal-, acid-, and base-free 2-(bromomethyl)naphthalene (2-BMN)-promoted organocatalytic Cloke-Wilson rearrangement of chain doubly activated cyclopropanes for the construction of 2,3-dihydrofurans via a carbocation-initiated tandem intramolecular ring-opening/recyclization process. The strategy is especially suitable for the construction of furan units in complex molecules, providing a solution to the problem of heavy-metal residues in dihydrofuran-containing drugs synthesized by traditional metal-based protocols. Thus, it is of potential interest in synthetic and medicinal chemistry.