6533b82ffe1ef96bd1295b66

RESEARCH PRODUCT

Organocatalytic enantioselective functionalization of indoles in the carbocyclic ring with cyclic imines

Arturo TortosaCarlos VilaJosé R. PedroM. Carmen MuñozGonzalo Blay

subject

Alkylation02 engineering and technologyAlkylation010402 general chemistryRing (chemistry)01 natural sciencesHydroxyindolesCatalysisKetiminesReaccions químiqueschemistry.chemical_compoundMaterials ChemistryFriedel-Crafts reactionBifunctionalFriedel–Crafts reactionConstructionAsymmetric-SynthesisChemistryInhibitorsEnantioselective synthesisGeneral Chemistry021001 nanoscience & nanotechnologyCombinatorial chemistry0104 chemical sciencesFISICA APLICADASurface modification0210 nano-technologyQuímica orgànicaDerivatives

description

[EN] An organocatalytic enantioselective functionalization in the carbocyclic ring of indoles with benzoxathiazine 2,2-dioxides is described using a quinine-derived bifunctional organocatalyst. This aza-Friedel-Crafts reaction provides 4-indolyl, 5-indolyl and 7-indolyl sulfamidate derivatives in good yields (up to 99%) and with moderate to high enantioselectivities (up to 86% ee).

10.1039/c8nj05577ghttps://doi.org/10.1039/C8NJ05577G