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exo-2,3-Epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides: versatile starting materials for the preparation of oxazaheterocyclic cage compounds

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Abstract

A convenient method is reported for the synthesis of N-substituted exo-2-hydroxy-6-aza-4-oxatetracyclo[5.2.1.13,508,9]undecan-7-ones, exo-2-hydroxy-6-aza-4-oxatetracyclo[5.2.1.13,508,9]undecanes, and endo-8,exo-9-dihydroxy-4-azatricyclo[5.2.1.02,6]decanes in high to moderate yields. The method involves treatment of easily available exo-2,3-epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides with LiAlH4.

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Acknowledgments

This work was financially supported by a President of Ukraine grant for young scientists GP/F49/080 (Dr. Vitaliy Palchikov). We are grateful to Dr. Andriy Kasyan (ProBioGen AG, Germany), Dr. Barbara Odell, and Dr. Colin Sparrow (University of Oxford, UK) for NMR and HRMS support. The authors are indebted to Dr. Oleksandr Zhurakovskyi (University of Oxford, UK) for the thorough revision of the manuscript.

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Authors and Affiliations

  1. Department of Chemistry, Oles Honchar Dnipropetrovsk National University, Dnipropetrovsk, Ukraine

    Vitaliy A. Palchikov, Igor N. Tarabara & Liliya I. Kasyan

  2. Ukrainian State University of Chemical Technology, Dnipropetrovsk, Ukraine

    Oxana V. Krishchik

  3. Institute for Single Crystals NAS of Ukraine, Kharkov, Ukraine

    Irina V. Omelchenko, Svetlana V. Shishkina & Oleg V. Shishkin

Authors
  1. Vitaliy A. Palchikov
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  2. Igor N. Tarabara
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  3. Oxana V. Krishchik
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  4. Irina V. Omelchenko
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  5. Svetlana V. Shishkina
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  6. Oleg V. Shishkin
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  7. Liliya I. Kasyan
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Corresponding author

Correspondence to Vitaliy A. Palchikov.

Additional information

Deceased: L. I. Kasyan.

This paper is a part of the PhD thesis by V. A. Palchikov.

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Palchikov, V.A., Tarabara, I.N., Krishchik, O.V. et al. exo-2,3-Epoxybicyclo[2.2.1]heptan-endo-5,6-dicarboximides: versatile starting materials for the preparation of oxazaheterocyclic cage compounds. Monatsh Chem 145, 1155–1163 (2014). https://doi.org/10.1007/s00706-014-1192-y

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  • DOI: https://doi.org/10.1007/s00706-014-1192-y

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