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Chiral imines and amines based on 2-hydroxypinan-3-one

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The new chiral derivatives of benzylamine and 2α-hydroxypinan-3-one (1R,2R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (2), (1S,2S,3S,5S)-3-(benzylamino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (3), and (1R,2R,3R,5R)-3-[(1S)-α-methylbenzylamino]-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol (4) were synthesized and characterized. It was shown that reduction of the benzylimines by sodium triacetoxyborohydride formed stereoselectively 3β-substituted pinanamines.

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Authors and Affiliations

  1. Institute of Chemistry, Komi Scientific Center, Ural Branch, Russian Academy of Sciences, 167982, Syktyvkar, Russia

    Ya. A. Gur’eva, L. L. Frolova, I. N. Alekseev & A. V. Kuchin

  2. Syktyvkar State University, 167023, Syktyvkar, Ul. Petrozavodskaya, 120, Russia

    O. A. Zalevskaya

Authors
  1. Ya. A. Gur’eva
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  2. O. A. Zalevskaya
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  3. L. L. Frolova
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  4. I. N. Alekseev
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  5. A. V. Kuchin
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Corresponding author

Correspondence to Ya. A. Gur’eva.

Additional information

Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 783–785, November–December, 2010.

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Gur’eva, Y.A., Zalevskaya, O.A., Frolova, L.L. et al. Chiral imines and amines based on 2-hydroxypinan-3-one. Chem Nat Compd 46, 920–923 (2011). https://doi.org/10.1007/s10600-011-9783-x

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  • DOI: https://doi.org/10.1007/s10600-011-9783-x

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