Organocatalytic Regio- and Asymmetric C-Selective SNAr ReactionsStereoselective Synthesis of Optically Active Spiro-pyrrolidone-3,3‘-oxoindoles
- 23 February 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (11) , 3670-3671
- https://doi.org/10.1021/ja050200g
Abstract
The first example of catalytic enantioselective nucleophilic aromatic substitution of β-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.Keywords
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