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Stereochemistry of Tropine and pseudo-Tropine

Nature volume 169, pages 462–463 (1952)Cite this article

Abstract

ACYL migration N → O was used for the determination of the configuration of the diastereomeric 1.2-amino-alcohols, for example, ephedrine1, chloromycetin2, as well as for that of the alicyclic amino-alcohols (2-amino-cyclohexanol and pentanols) containing flexible3a or rigid3b ring systems by Fodor and Kiss. More recently, McCasland4 elucidated the configuration of the epimeric inosamines by the same means.

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References

  1. Fodor, G., et al., (a) J. Org. Chem., 14, 337 (1949); (b) ibid., 15, 226 (1950).

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  2. Fodor, G., Kiss, J., and Sallay, I., J. Chem. Soc., 1858 (1951).

  3. Fodor, G., and Kiss, J., (a) Nature, 164, 917 (1949); (b) Research, 4, 382 (1951); (c) Research, 4, 381 (1951).

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  7. Prepared by Polonovsky, M., and Polonovski, M., Bull. Soc. Chim., 39, 1147 (1926), who suggested it had the structure of an acyl-amide salt; our electrometric titrations proved the correctness of this assumption.

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Authors and Affiliations

  1. Institute of Organic Chemistry, University, Szeged,

    G. FODOR & K. NÁDOR

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  1. G. FODOR
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  2. K. NÁDOR
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FODOR, G., NÁDOR, K. Stereochemistry of Tropine and pseudo-Tropine. Nature 169, 462–463 (1952). https://doi.org/10.1038/169462a0

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