6533b7cefe1ef96bd1256f39

RESEARCH PRODUCT

Catalytic enantioselective Friedel–Crafts alkylation at the 2-position of indole with simple enones

Gonzalo BlayIsabel FernándezCarlos VilaJosé R. Pedro

subject

Indole testZirconiumChemistryOrganic ChemistryDrug DiscoveryEnantioselective synthesisOrganic chemistrychemistry.chemical_elementAlkylationBiochemistryBenzoquinoneFriedel–Crafts reactionCatalysis

description

Abstract A procedure for the enantioselective alkylation of indole at the 2-position with simple non-chelating enones is described for the first time. Reaction between 4,7-dihydroindole and enones in the presence of zirconium(IV)–BINOL complexes, followed by a p -benzoquinone oxidation gives indoles alkylated at the 2-position with good yields and moderate enantioselectivities.

https://doi.org/10.1016/j.tetlet.2007.07.090