Synthesis 2013; 45(2): 225-230
DOI: 10.1055/s-0032-1316831
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isomeric 6-Trifluoromethyl-3-azabicyclo[3.1.0]hexanes: Conformationally Restricted Analogues of 4-Trifluoromethylpiperidine

Authors

  • Olexiy S. Artamonov

    a   Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska Street 5, Kyiv-94 02660, Ukraine
  • Evgeniy Y. Slobodyanyuk

    b   Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    eMail: Pavel.Mykhailiuk@gmail.com
    c   Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
  • Oleg V. Shishkin

    d   STC, ‘Institute for Single Crystals,’ National Academy of Science, 60 Lenina ave., Kharkiv 61001, Ukraine
  • Igor V. Komarov

    b   Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    eMail: Pavel.Mykhailiuk@gmail.com
    c   Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
  • Pavel K. Mykhailiuk*

    b   Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine    eMail: Pavel.Mykhailiuk@gmail.com
    c   Department of Chemistry, and Kyiv National Taras Shevchenko University, Vul. Volodymyrska 64, Kyiv 01033, Ukraine
Weitere Informationen

Publikationsverlauf

Received: 02. November 2012

Accepted after revision: 29. November 2012

Publikationsdatum:
18. Dezember 2012 (online)


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Abstract

Two isomeric conformationally restricted analogues of 4-trifluoromethylpiperidine were designed. The synthesis was performed in four steps from commercially available N-benzylmaleimide. The key reaction was the [3+2] cycloaddition between trifluoromethyldiazomethane and N-benzylmaleimide.

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