Journal
CHEMICAL SCIENCE
Volume 9, Issue 3, Pages 754-759Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc04723a
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Funding
- EPSRC
- Eli Lilly
- Engineering and Physical Sciences Research Council [EP/P001386/1, EP/M005062/1] Funding Source: researchfish
- EPSRC [EP/P001386/1, EP/M005062/1, 1712689] Funding Source: UKRI
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A dual vicinal functionalisation cascade involving the union of heterocycles and allyl sulfoxides is described. In particular, the approach provides efficient one-step access to biologically relevant and synthetically important C3 thio, C2 carbo substituted indoles. The reaction operates under mild, metal free conditions and without directing groups, via an interrupted Pummerer coupling of activated allyl sulfoxides, generating allyl heteroaryl sulfonium salts that are predisposed to a charge accelerated [3,3]-sigmatropic rearrangement.
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