Solution phase synthesis of a spiro[pyrrolidine-2,3′-oxindole] library via a three component 1,3-dipolar cycloaddition reaction

A combinatorial library of 26,500 spiro[pyrrolidine-2,3′-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a trans-chalcone...

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Bibliographic Details
Published in:Tetrahedron letters 1998-04, Vol.39 (16), p.2235-2238
Main Authors: Fokas, Demosthenes, Ryan, William J., Casebier, David S., Coffen, David L.
Format: Article
Language:English
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Summary:A combinatorial library of 26,500 spiro[pyrrolidine-2,3′-oxindoles] was prepared in a single-compound format by a facile intermolecular 1,3-dipolar cycloaddition. An azomethine ylide, generated by the decarboxylative condensation of an isatin 1 with an α-amino acid 2, was trapped by a trans-chalcone 3 to afford heterocycles of the general structure 4. The regio- and stereochemistry of a representative product was determined by single crystal X-ray structure. Spiropyrrolidines of the general structure (4) are prepared in one pot from isatins (1), amino acids (2) and chalcones (3).
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00234-2