4.6 Article

One-step formation of dihydrofuranoindoline cores promoted by a hypervalent iodine reagent

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 15, Issue 17, Pages 3736-3741

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c7ob00326a

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Funding

  1. Natural Sciences and Engineering Research Council of Canada (NSERC)
  2. Canada Foundation for Innovation (CFI)
  3. provincial government of Quebec (FQRNT and CCVC)

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Treatment of various substituted anilines containing a sulfonyl group in the presence of a hypervalent iodine reagent, a perfluorinated alcohol and furan promotes a formal dearomatizing [2 + 3] cycloaddition process, leading to a dihydrofuranoindoline core in useful yields. Thereafter, these functionalized systems can be used for further transformations, yielding potential key intermediates for the total synthesis of complex natural products.

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