Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process.
Copper-mediated construction of spirocyclic bis-oxindoles via a double C-H, Ar-H coupling process.
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DOI：
10.1021/ol5024129
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发表时间：
2014-09
期刊：
影响因子：
5.2
通讯作者：
Pauline Drouhin;Timothy E. Hurst;A. Whitwood;R. Taylor
中科院分区：
文献类型：
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作者：
Pauline Drouhin;Timothy E. Hurst;A. Whitwood;R. Taylor
本文描述了一种双C-H，Ar-H偶合反应，将双苯胺转化为螺环双羟吲哚，并以非对映选择性的方式在羟吲哚3-位同时形成两个全碳季中心。最佳环化条件利用化学计量的Cu（0Ac）2·H2O/KOtBu在DMF中在110 °C下，并已被应用于制备一系列结构多样的双螺羟吲哚，产率相当高（28-77%）;该方法还被扩展到制备由官能化的无环碳链连接的双羟吲哚。
A double C-H, Ar-H coupling process for the conversion of bis-anilides into spirocyclic bis-oxindoles, enabling the concomitant formation of two all-carbon quaternary centers at oxindole 3-positions in a diastereoselective manner, is described. The optimum cyclization conditions utilize stoichiometric Cu(OAc)2·H2O/KOtBu in DMF at 110 °C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28-77%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.