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RESEARCH PRODUCT
ChemInform Abstract: Enantioselective Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones.
Carlos VilaIsabel FernándezGonzalo BlayAlicia MonleonJosé R. Pedrosubject
chemistry.chemical_compoundTrifluoromethylchemistryEnantioselective synthesisOrganic chemistryMoietyGeneral MedicineAlkylationFriedel–Crafts reactionStereocenterCatalysisPyrroledescription
The first catalytic enantioselective Friedel−Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones to give pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety bearing a quaternary stereogenic center is described. The reaction is achieved in the presence of a 3,3′-dibromo-BINOL-Zr(IV) complex to give the expected products with high yields (up to 98%) and good enantioselectivities (up to 93% ee). The absolute stereochemistry of the products has been determined by chemical correlation.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2009-06-16 | ChemInform |