Volume 17, Issue 1 pp. 61-65

Research Article

Free to Read

Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones^†

Malika Berredjem,

Malika Berredjem

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Search for more papers by this author

Zine Regainia,

Zine Regainia

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Search for more papers by this author

Georges Dewynter,

Georges Dewynter

UMR 5810 Laboratoire des Aminoacides, Peptides et Protéines CC 019, Universités Montpellier-I et II, place E. Bataillon, 34095 Montpellier cedex 5, France

Search for more papers by this author

Jean Louis Montero,

Jean Louis Montero

UMR 5032 Laboratoire de Chimie Biomoléculaire, Universités Montpellier II, ENSCM, 8 rue de l'Ecole Normale, 34096 Montpellier cedex, France

Search for more papers by this author

Nour-Eddine Aouf,

Corresponding Author

Nour-Eddine Aouf

[email protected]

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, AlgérieSearch for more papers by this author

Malika Berredjem,

Malika Berredjem

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Search for more papers by this author

Zine Regainia,

Zine Regainia

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Search for more papers by this author

Georges Dewynter,

Georges Dewynter

UMR 5810 Laboratoire des Aminoacides, Peptides et Protéines CC 019, Universités Montpellier-I et II, place E. Bataillon, 34095 Montpellier cedex 5, France

Search for more papers by this author

Jean Louis Montero,

Jean Louis Montero

UMR 5032 Laboratoire de Chimie Biomoléculaire, Universités Montpellier II, ENSCM, 8 rue de l'Ecole Normale, 34096 Montpellier cedex, France

Search for more papers by this author

Nour-Eddine Aouf,

Corresponding Author

Nour-Eddine Aouf

[email protected]

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, Algérie

Laboratoire de Chimie Organique Appliquée, Groupe de Chimie Bioorganique, Université d'Annaba, BP12, AlgérieSearch for more papers by this author

First published: 30 January 2006

https://doi.org/10.1002/hc.20183

Citations: 12

^†

To Dr Kamel Seghoum, in memoriam.

About

PDF

Tools

Share a link

Email
Wechat
Bluesky

Abstract

A series of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones were synthesized starting from 2-aminoalcohols, sulfuryl chloride, and diethyl carbonate. This method utilizes natural amino acids as a source of chirality for the preparation of oxazolidinones. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:61–65, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20183

REFERENCE

1Bowerscock, T. L.;Salmon, S. A.;Portis, E. S.;Prescott, J. F.;Robinson, D. A.;Ford, C. W.;Watts, J. L.Antimicrob Agents Chemother2004, 44, 1367
10.1128/AAC.44.5.1367-1369.2000
Web of Science® Google Scholar
2Skold, O.Acta Vert Scand2000, 23
CAS Web of Science® Google Scholar
3Johnson, A. P.;Warner, M.;Livermore, D. M.J Antimicrob Chemother2000, 45, 953.
Google Scholar
4Philips, O. A.;Udo, E. E.;Ali, A. A.;Al-Hassawi, N.Bioorg Med Chem2002, 10, 1.
10.1016/S0968-0896(01)00405-9
PubMed Web of Science® Google Scholar
5Ciske, F. L.;Barbachyn, M. R.;Genin, M. J.;Grega, K. C.;Lee, C. S.;Dolak, L. A.Seest, E. P.;Watt, W.;Adams, W. J.;Friis, M. J.;Ford, C. W.;Zurenko, G. E.Bioorg Med Chem Lett2003, 13(23), 4235
10.1016/j.bmcl.2003.07.029
CAS PubMed Web of Science® Google Scholar
6Cynamon, M. H.;Klemens, S. P.;Sharpe, C. A.Antimicrob Agents Chemother1999, 43, 1189
10.1128/AAC.43.5.1189
CAS PubMed Web of Science® Google Scholar
7Ager, J. A.;Prakach, I;Schaad, D. R.Aldrichim Acta1997, 30, 3–12
CAS Web of Science® Google Scholar
8Ager, J. A.;Prakach, I;Schaad, D. R.Chem Rev1996, 96, 835
10.1021/cr9500038
CAS PubMed Web of Science® Google Scholar
9Evans, D. A.Aldrichim Acta1982, 15, 23
CAS Google Scholar
10Evans, D. A.;Dow. R. L.Tetrahedron Lett1986, 27, 1007
10.1016/S0040-4039(86)80034-X
CAS Web of Science® Google Scholar
11Wu, Y.;Shen, X.Tetrahedron:Asymmetry2000, 11, 1455
Google Scholar
12Barta, S. J.;Silder, D. R.;Somerville, K. B.;Weissman, S. A.;Larsen, R. D.;Reider, P. J.J Org Chem2000, 2, 2821
CAS PubMed Web of Science® Google Scholar
13Katz, S. J.;Bergmeier, S. C.Tetrahedron Lett2002, 43, 557
10.1016/S0040-4039(01)02218-3
CAS Web of Science® Google Scholar
14Park, C. S.;Kim, M. S.;Sim, T. B.;Pyun, D. K.;Lee, C. H.;Choi, D.;Lee, W. K.J Org Chem2003, 68, 43
10.1021/jo025545l
CAS PubMed Web of Science® Google Scholar
15Sim, T. B.;Kang, S. H.;Lee, K. S.;Lee, W. K.J Org Chem2003, 68, 104
10.1021/jo0261911
CAS PubMed Web of Science® Google Scholar
16Dewynter, G.;Abdaoui, M.;Toupet, L.;Montero, J.-L.Tetrahedron Lett1997, 38, 8691
10.1016/S0040-4039(97)10336-7
CAS Web of Science® Google Scholar
17Lee, S. G.;Lin, C. W.;Kim, D. C.;Lee, J. K.Tetrahedron:Asymmetry2000, 11, 1455
10.1016/S0957-4166(00)00086-0
CAS Web of Science® Google Scholar
18Berredjem, M.;Winum, J-Y.;Toupet, L.Masmoudi, O.;Aouf, N.;Montero, J-L.Synthetic Commun2004, 34, 1653
10.1081/SCC-120030753
CAS Web of Science® Google Scholar
19 L. Paquette (Ed.); Encyclopedia of Reagents for Organic Synthesis;Wiley: Chischester, UK,1995; BOP-Cl, Vol. 1, p. 543; CDI, Vol. 2, p. 1006; sulfuryl diimidazole, Vol. 7, p. 4709
Google Scholar
20Gage, J. R.;Evans, D. A.Org Synth1990, 68, 77.
10.15227/orgsyn.068.0077
CAS Web of Science® Google Scholar

Citing Literature

All articles

Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones^†

Abstract

REFERENCE

Citing Literature

References

Information

About Wiley Online Library

Help & Support

Opportunities

Connect with Wiley

Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones†

Abstract

REFERENCE

Citing Literature

References

Related

Information

Simple and efficient synthesis of new chiral N,N′-sulfonyl bis-oxazolidin-2-ones^†