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(S)-(−)-α-Methylbenzylamine as chiral auxiliary in the synthesis of (+)-lortalamine

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Abstract

(+)-Lortalamine was synthesised using (S)-(−)-α-methylbenzylamine as a chiral auxiliary. The stereochemistry of an intermediate compound was established on the basis of X-ray crystallography, allowing unambiguous assignment of the absolute configuration.

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References

  1. Briet P, Berthelon JJ, Depin JC (1980) US Patent 4.201.783

  2. Ding Y-S, Lin K-S (2005) Bioorg Med Chem 13:4658–4666

    Article  Google Scholar 

  3. Sanger DJ, Depoortere R, Perrault G (1996) Behav Pharmacol 7:477–482

    CAS  Google Scholar 

  4. Depin JC, Betbeder-Matibet A, Bonhomme Y, Muller AJ, Berthelon JJ (1985) Arzneim-Forsch/Drug Res 35 (II), 11:1655–1662

    Google Scholar 

  5. Juaristi E, Escalante J, León-Romo JL, Reyes A (1998) Tetrahedron Asymmetry 9:715–740

    Article  CAS  Google Scholar 

  6. Juaristi E, León-Romo JL, Reyes A, Escalante J (1999) Tetrahedron Asymmetry 10:2441–2495

    Article  CAS  Google Scholar 

  7. Ziółkowski M, Czarnocki Z, Leniewski A, Maurin JK (1999) Tetrahedron Asymmetry 10:3371–3380

    Article  Google Scholar 

  8. Kuehne ME, Matson PA, Bornman WG (1991) J Org Chem 56:513

    Article  CAS  Google Scholar 

  9. Horning EC, Horning MG, Dimmig DA (1955) Org Synth Collect III:165

    Google Scholar 

  10. Biała J, Czarnocki Z, Maurin JK (2002) Tetrahedron Asymmetry 13:1021

    Article  Google Scholar 

  11. Sheldrick GM (1990) Acta Crystallogr A46:467–473

    CAS  Google Scholar 

  12. Sheldrick GM, SHELXL-97. Program for the refinement of crystal structures, University of Göttingen, Germany

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Acknowledgment

We acknowledge financial support from grant PBZ-KBN-126/T09/2004/13.

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Authors and Affiliations

  1. Faculty of Chemistry, Warsaw University, Pasteura 1, 02-093, Warsaw, Poland

    Jolanta Pawłowska, Krzysztof K. Krawczyk, Krystyna Wojtasiewicz & Zbigniew Czarnocki

  2. National Medicines Institute, Chełmska 30/34, 00-725, Warsaw, Poland

    Jan K. Maurin

  3. Institute of Atomic Energy, 05-400, Otwock-Świerk, Poland

    Jan K. Maurin

Authors
  1. Jolanta Pawłowska
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  2. Krzysztof K. Krawczyk
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  3. Krystyna Wojtasiewicz
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  4. Jan K. Maurin
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  5. Zbigniew Czarnocki
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Corresponding author

Correspondence to Zbigniew Czarnocki.

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Pawłowska, J., Krawczyk, K.K., Wojtasiewicz, K. et al. (S)-(−)-α-Methylbenzylamine as chiral auxiliary in the synthesis of (+)-lortalamine. Monatsh Chem 140, 83–86 (2009). https://doi.org/10.1007/s00706-008-0017-2

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  • DOI: https://doi.org/10.1007/s00706-008-0017-2

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