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Synthesis 1997; 1997(11): 1291-1295
DOI: 10.1055/s-1997-1342
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Synthesis of Polyfunctionalized 2,5-Dicarboxylated Pyrrolidine Derivatives by 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides

Claudia Wittland, Ulrich Flörke, Nikolaus Risch*
  • *Universität-GH Paderborn, Fachbereich für Chemie und Chemietechnik, Warburger Str. 100, D-33098 Paderborn, Germany, Fax +49(5251)603245; E-mail: nr@chemie.uni-paderborn.de
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Publikationsdatum:
31. Dezember 2000 (online)

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The stereoselective synthesis of 2,5-dicarboxylated pyrrolidine derivatives by 1,3-dipolar cycloaddition reactions of in situ generated azomethine ylides from inexpensive starting materials is described. The C2-symmetric cycloadducts are interesting precursors for new chiral auxiliaries and are transformed easily into other highly functionalized proline derivatives. The configuration of the cycloadducts has been determined by NMR data and single crystal X-ray structure analyses. The syntheses of pyrrolidine-2,3,4,5-tetracarboxylic acid and 2,3,4,5-tetrahydroxymethylpyrrolidine are also reported.

azomethine ylides - 1,3-dipolar cycloadditions - pyrrolidines - C2-symmetric auxiliaries