Copper-Mediated Construction of Spirocyclic Bis-oxindoles via a Double C鈥揌, Ar鈥揌 Coupling Process

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• 作者：Pauline Drouhin ; Timothy E. Hurst ; Adrian C. Whitwood ; Richard J. K. Taylor
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：September 19, 2014
• 年：2014
• 卷：16
• 期：18
• 页码：4900-4903
• 全文大小：378K
• ISSN：1523-7052

文摘

A double C鈥揌, Ar鈥揌 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路H₂O/KOtBu in DMF at 110 掳C and have been applied to prepare a range of structurally diverse bis-spirooxindoles in fair to good yields (28鈥?7%); the method has also been extended to prepare bis-oxindoles linked by a functionalized acyclic carbon chain.