Organocatalytic regio- and asymmetric C-selective SNAr reactions-stereoselective synthesis of optically active spiro-pyrrolidone-3,3 '-oxoindoles

The first example of catalytic enantioselective nucleophilic aromatic substitution of -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. Copyright © 2005 American Chemical Society.