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Enantioselective Zirconium-Catalyzed Friedel−Crafts Alkylation of Pyrrole with Trifluoromethyl Ketones

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journal contribution
posted on 2009-01-15, 00:00 authored by Gonzalo Blay, Isabel Fernández, Alicia Monleón, José R. Pedro, Carlos Vila
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.

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