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Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbonsäuren. Chiralitätstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen

Heterocyclic compounds from sugars, XV: On the configuration of chiral C-2 substituted 1,3-thiazolidine-4-carboxylic acids. Chirality transfer to C-3 of 3,4-dihydro-1H-pyrrolo[1,2-c]thiazoles

  • Organische Chemie Und Biochemie
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Summary

5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids,1 in [3+2]-cycloaddition reactions via mesoionic oxazolone (“münchnone”) intermediates. The chirality at C-4 of the starting carboxylic acids1 is eliminated in the products3, and the chirality at C-3 (C-2 in the starting carboxylic acids1) can thus be determined through chiroptical measurements. Several representatives of the ring system3 have been characterised through1H- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.

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Authors and Affiliations

  1. Lehrstuhl für Organische Chemie, Lajos-Kossuth-Universität, H-4010, Debrecen, Ungarn

    Z. Györgydeák & L. Szilágyi

  2. Lehrstuhl für Orgnische Chemie, Loránd-Eötvös-Universität, H-1518, Budapest, Ungarn

    J. Kajtár

  3. Zentralforschungsinstitut für Chemie, Ungarische Akademie der Wissenschaften, H-1525, Budapest, Ungarn

    G. Argay & A. Kálmán

Authors
  1. Z. Györgydeák
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  2. L. Szilágyi
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  3. J. Kajtár
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  4. G. Argay
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  5. A. Kálmán
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Györgydeák, Z., Szilágyi, L., Kajtár, J. et al. Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbonsäuren. Chiralitätstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen. Monatsh Chem 125, 189–208 (1994). https://doi.org/10.1007/BF00818164

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  • DOI: https://doi.org/10.1007/BF00818164

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