title: Organocatalytic regio- and asymmetric C-selective S(N)Ar reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3'-oxoindoles.
abstract: The first example of catalytic enantioselective nucleophilic aromatic substitution of beta-dicarbonyl compounds is presented. An O-benzoylated cinchona alkaloid derivative catalyst gave a selective C-arylation reaction compared to, e.g., the corresponding benzylated catalyst which provided a 1:1 mixture of the C- and O-arylation products. The reaction proceeds well for various aromatic compounds with different 1,3-dicarbonyl compounds, and the optically active products are obtained in very high yields and with up to 92% ee. One further scope of the organocatalytic enantioselective nucleophilic aromatic substitution reaction is demonstrated by the synthesis of the optically active spiro-pyrrolidone-3,3'-oxoindole structure.
authors.affiliation: Danish National Research Foundation, Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
authors.forename: Marco
authors.initials: M
authors.lastname: Bella
authors.forename: Sara
authors.initials: S
authors.lastname: Kobbelgaard
authors.forename: Karl Anker
authors.initials: KA
authors.lastname: Jørgensen