Journal
ORGANIC LETTERS
Volume 20, Issue 11, Pages 3349-3353Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01248
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Funding
- EPSRC [EP/M018601/01]
- University of York
- Leverhulme Trust [ECF-2015-13]
- EPSRC [EP/M018601/1] Funding Source: UKRI
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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.
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