Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor–Acceptor Cyclopropanes,Journal of the American Chemical Society

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Copper-Catalyzed Highly Enantioselective Cyclopentannulation of Indoles with Donor–Acceptor Cyclopropanes
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2013-05-17 , DOI: 10.1021/ja4042127
Hu Xiong _{1,

2} , Hao Xu ₁ , Saihu Liao ₁ , Zuowei Xie _{2,

3} , Yong Tang ₁

Affiliation

A highly diastereo- and enantioselective BOX/Cu(II)-catalyzed C2,C3-cyclopentannulation of indoles with donor-acceptor cyclopropanes has been developed on the basis of asymmetric formal [3 + 2] cycloaddition of indoles. This reaction provides rapid and facile access to a series of enantioenriched cyclopenta-fused indoline products and can be further extended to the construction of tetracyclic pyrroloindolines. The synthetic potential of the reaction was demonstrated in a four-step synthesis of the core structure of borreverine.

中文翻译：

铜催化的吲哚与供体-受体环丙烷的高对映选择性环戊烷化

在吲哚的不对称形式 [3 + 2] 环加成的基础上，开发了一种高度非对映选择性和对映选择性 BOX/Cu(II) 催化的吲哚与供体-受体环丙烷的 C2,C3-环戊环化反应。该反应提供了对一系列对映体富集的环戊二烯稠合二氢吲哚产物的快速简便的获取，并可进一步扩展到四环吡咯并二氢吲哚的构建。该反应的合成潜力在硼酸碱的核心结构的四步合成中得到了证明。

更新日期：2013-05-17

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