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Dearomatizing Spiroannulation Reagents: Direct Access to Spirocycles from Indoles and Dihalides

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JournalOrganic Letters
DateAccepted/In press - 4 May 2018
DateE-pub ahead of print (current) - 10 May 2018
Number of pages5
Early online date10/05/18
Original languageEnglish


Unfunctionalized indoles can be directly converted into 3,3'-spirocyclic indolenines and indolines upon reaction with electrophilic dihalides in the presence of t-BuOK/BEt3. This double C-C bond forming reaction, which simultaneously generates a quaternary spirocyclic center, typically proceeds in high yield and has good functional group tolerance. In contrast to existing dearomatizing spirocyclization approaches, there is no need to prepare a prefunctionalized aromatic precursor, enabling faster access to valuable spirocyclic products from simple, commercially available aromatics in one step.

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