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

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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.

Original languageEnglish
Number of pages5
JournalOrganic Letters
Early online date10 May 2018
Publication statusE-pub ahead of print - 10 May 2018

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