Skip to main content
Log in

Enantiomere und diastereomere 2-Methoxymethyl-pyrrolidin-1-dithiocarbonsäureester

Enantiomeric and diastereomeric esters of 2-methoxymethyl-pyrrolidine-1-dithiocarboxylic acids

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Formation of the 2-methoxymethyl-pyrrolidine-1-dithiocarboxylates2–4 and alkylation of2 and3 were studied. Enantiomeric and diastereomeric derivatives of4, the preparation of diastereomeric mixtures of4 by alkylation of3 in the presence of strong bases, and formation of6 by phase transfer alkylation of2 are described. The two enantiomers of 2-(4-bromophenyl)-2-oxo-ethyl 2-methoxymethylpyrrolidine-1-dithiocarboxylate2 have been characterized by X-ray analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literatur

  1. Corey EJ, Cimprich KA (1992) Tetrahedron Lett33: 4099

    Google Scholar 

  2. Hajos A (1981) Reduktion von Dithiokohlensäure-ester-amiden, Houben-Weyl, Methoden der organischen Chemie, vol. 4/1d. Thieme, Stuttgart, p 344

    Google Scholar 

  3. Enders D (1983) Regio-, Diastereo-, and Enantioselective C-C Coupling Reactions using Metalated Hydrazones, Formamides, Allylamides, and Aminonitriles. In: Nozaki H (ed) Current Trends in Organic Synthesis. Pergamon Press, Oxford, pp 151–167

    Google Scholar 

  4. Ahlbrecht H, Enders D, Santowski L, Zimmermann G (1989) Chem Ber122: 1995

    Google Scholar 

  5. Reich HJ, Bowe MD (1990) J Am Chem Soc112: 8994

    Google Scholar 

  6. Hoffmann RW, Rühl T, Harbach J (1992) Liebigs Ann Chem 725

  7. Ruhland T, Dress R, Hoffmann RW (1993) Angew Chem105: 1487

    Google Scholar 

  8. Reich HJ, Dykstra RR (1993) Angew Chem105: 1489

    Google Scholar 

  9. Reich HJ, Borst JB, Dykstra RR (1994) Tetrahedron50: 5869

    Google Scholar 

  10. Aggarwal VK (1994) Angew Chem106: 185

    Google Scholar 

  11. Chan TH, Hartley RC, Lamote S (1993) Tetrahedron Lett34: 1449

    Google Scholar 

  12. Chan TH, Wang D (1992) Chem Rev92: 995

    Google Scholar 

  13. Lamothe S, Cook KL, Chan TH (1992) Can J Chem70: 1733

    Google Scholar 

  14. Chan TH, Nwe KT (1992) J Org Chem57: 6107

    Google Scholar 

  15. Chan TH, Pellon P (1989) J Am Chem Soc111: 8737

    Google Scholar 

  16. Kaiser B, Hoppe D (1995) Angew Chem107: 344

    Google Scholar 

  17. Enders D, Klatt M (1996) Synthesis 1403

  18. Alker D, Doyle KJ, Harwood LM, McGregor A (1990) Tetrahedron: Asymmetrie1: 877

    Google Scholar 

  19. Dieter RK, Tokles M (1987) J Am Chem Soc109: 2040

    Google Scholar 

  20. Blarer SJ, Schweizer WB, Seebach D (1982) Helv Chim Acta65: 1637

    Google Scholar 

  21. Seebach D et al (1977) Helv Chim Acta60: 301

    Google Scholar 

  22. Hellrung B, Dölling W (1996) J Prakt Chem/Chem-Ztg338: 157

    Google Scholar 

  23. Zschage O, Schwark J-R, Hoppe D (1990) Angew Chem102: 336

    Google Scholar 

  24. Knochel P (1992) Angew Chem Int Ed Engl31: 1459

    Google Scholar 

  25. Enders D, Klatt M (1995) (S)-2-Methoxymethylpyrrolidine. in: Paquette LA (ed) Encyclopedia of Reagents for Organic Synthesis. Wiley, Chichester New York Brisbane Toronto Singapore, p 3367

    Google Scholar 

  26. Lamothe S, Cook KL, Chan TH (1992) Can J Chem70: 1733

    Google Scholar 

  27. Heathcock CH (1992) Modern Enolate Chemistry: Regio- and Stereoselective Formation of Enolates and the Consequence of Enolate Configuration on Subsequent Reactions. In: Scheffold R (ed) Modern Synthetic Methods 1992, vol 6. VCH, Basel, pp 1–102

    Google Scholar 

  28. Ahlbrecht H, Harbach J, Hoffmann RW, Ruhland T (1995) Liebigs Ann Chem 211

  29. Hoffmann RW, Rühl T, Harbach J (1992) Liebigs Ann Chem 725

  30. Hoffmann RW, Rühl T, Chemla F, Zahneisen T (1992) Liebigs Ann Chem 719

  31. Chan TH, Wang D (1989) Tetrahedron Lett30: 3041

    Google Scholar 

  32. Hoffmann RW (1993) Configurationally Stable and Configurationally Labile Chiral α-Substituted Organolithium Compounds in Stereoselective Transformations. In: Enders D, Gais H-J, Keim W (eds) Organic Synthesis via Organometallics. Vieweg, Braunschweig Wiesbaden, pp 79–91

    Google Scholar 

  33. Details zu den beiden Röntgenkristallstrukturanalysen von2 werden an anderer Stelle mitgeteilt

Download references

Author information

Authors and Affiliations

Authors

Additional information

Verstorben am 22. Juni 1996

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dölling, W., Hocke, I., Verjus, P. et al. Enantiomere und diastereomere 2-Methoxymethyl-pyrrolidin-1-dithiocarbonsäureester. Monatsh Chem 128, 881–891 (1997). https://doi.org/10.1007/BF00807097

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807097

Keywords

Navigation