6533b85cfe1ef96bd12bcb4a
RESEARCH PRODUCT
Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones
Alicia MonleonIsabel FernándezCarlos VilaGonzalo BlayJosé R. Pedrosubject
TrifluoromethylAlkylationOrganic ChemistryEnantioselective synthesisStereoisomerismKetonesAlkylationBiochemistryMedicinal chemistryCatalysisSubstrate SpecificityCatalysisStereocenterchemistry.chemical_compoundchemistryMoietyPyrrolesZirconiumPhysical and Theoretical ChemistryFriedel–Crafts reactionPyrroledescription
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 |
|---|---|---|---|---|
| 2009-01-09 | Organic Letters |