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Facile and Convenient One-Pot Process for the Synthesis of Spirooxindole Derivatives in High Optical Purity Using (−)-(S)-Brevicolline as an Organocatalyst

Author(s): Fliur Macaev | Natalia Sucman | Felix Shepeli | Marina Zveaghintseva | Vsevolod Pogrebnoi

Journal: Symmetry
ISSN 2073-8994

Volume: 3;
Issue: 2;
Start page: 165;
Date: 2011;
Original page

Keywords: organocatalyzed reactions | spiro[oxindole-3 | 4'-4'H-pyrane] | Brevicolline | Cinchonidine | Cinchonine

The paper presents an application of the asymmetry approach to spirooxindoles via Brevicolline, Cinchonidine or Cinchonine catalyzed one-pot multicomponent synthesis. Brevicolline, in comparison with Cinchonidine or Cinchonine, catalyzes the reaction of isatins, acetylacetone/ethyl 3-oxobutanoate and malononitrile, with the formation of spiro[oxindole-3,4'-4'H-pirane] derivatives in an optically active form in very good to excellent yields.
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