Skip to main content
SpringerLink
Log in

New Chiral Diamines of the Dioxolane Series: (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(diphenylaminomethyl)- 1,3-dioxolane and (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(methyl- aminomethyl)-1,3-dioxolane

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The reaction of sodium diphenylamide with 2,2-dimethyl-4,5-bis(tosyloxymethyl)-1,3-dioxolane gave (+)-(4S,5S)-2,2-dimethyl-4,5-bis(diphenylaminomethyl)-1,3-dioxolane, which was brought into complex formation with cobalt chloride. Treatment of 2,2-dimethyl-4,5-bis(tosyloxymethyl)-1,3-dioxolane with sodium N-methylanilide resulted in cleavage of the SÄO bond in the p-toluenesulfonate moiety with formation of N-methyl-N-phenyl-p-toluenesulfonamide and 4,5-bis(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane disodium salt. Diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate reacted with methylamine to give the corresponding dicarboxamide which was reduced with lithium aluminum hydride to (4S,5S)-2,2-dimethyl-4,5-bis(methylaminomethyl)-1,3-dioxolane having chiral carbon and nitrogen atoms.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. Nindakova, L.O., Shainyan, B.A., and Albanov, A.I., Izv. Ross. Akad Nauk, Ser. Khim., 2001, vol. 10, pp. 1777-1782.

    Google Scholar 

  2. Shainyan, B.A., Ustinov, M.V., and Nindakova, L.O., Russ. J. Org. Chem., 2001, vol. 37, no. 12, pp. 1757-1761.

    Google Scholar 

  3. Shainyan, B.A., Ustinov, M.V., Bel'skii, V.K., and Nindakova, L.O., Russ. J. Org. Chem., 2002, vol. 38, no. 1, pp. 104-110.

    Google Scholar 

  4. Lever, E., Inorganic Electronic Spectroscopy, Amsterdam: Elsevier, 1984, 2nd ed.

    Google Scholar 

  5. Gillam and Stern's Introduction to Electronic Absorp-tion Spectroscopy in Organic Chemistry, Stern, E.S. and Timmons, C.J., Eds., London: Arnold, 1970, 3rd ed.

    Google Scholar 

  6. Gur'yanova, E.N., Gol'dshtein, I.P., and Romm, I.P., Donorno-aktseptornaya svyaz' (The Donor–Acceptor Bond), Moscow: Khimiya, 1973.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    B. A. Shainyan, L. O. Nindakova, M. V. Ustinov, N. N. Chipanina & L. V. Sherstyannikova

Authors
  1. B. A. Shainyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. O. Nindakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. V. Ustinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. N. Chipanina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. L. V. Sherstyannikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shainyan, B.A., Nindakova, L.O., Ustinov, M.V. et al. New Chiral Diamines of the Dioxolane Series: (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(diphenylaminomethyl)- 1,3-dioxolane and (+)-(4S,5S)-2,2-Dimethyl-4,5-bis(methyl- aminomethyl)-1,3-dioxolane. Russian Journal of Organic Chemistry 38, 1802–1805 (2002). https://doi.org/10.1023/A:1022528016140

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1022528016140

Keywords

Search

Navigation