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

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JournalOrganic Letters
DateE-pub ahead of print - 8 Sep 2014
DatePublished (current) - 18 Sep 2014
Issue number18
Volume16
Number of pages4
Pages (from-to)4900-4903
Early online date8/09/14
Original languageEnglish

Abstract

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.

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