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RESEARCH PRODUCT

ChemInform Abstract: Enantioselective Synthesis of Tertiary Alcohols Through a Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrroles with α-Ketoesters.

Carlos VilaGonzalo BlayJosé R. PedroM. Carmen MuñozIsabel FernándezAlejandro Recuenco

subject

ZirconiumchemistryEnantioselective synthesischemistry.chemical_elementOrganic chemistryGeneral MedicineAlkylationFriedel–Crafts reactionTertiary alcoholsPyrrole derivativesCatalysis

description

Chiral complexes of 1,1′-bi-2-naphthol-based ligands with zirconium tert-butoxide catalyze the Friedel–Crafts alkylation of pyrroles with α-ketoesters to afford tertiary alcohols in good yields and ee up to 98%. The reaction is also of application to 4,7-dihydroindole to give C2-alkylated indoles after oxidation with p-benzoquinone.

https://doi.org/10.1002/chin.201149106