Issue 14, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides: a computational study†

F. Javier Casado-Bellver,a   M. Eugenia González-Rosende,*b   Amparo Asensio,a   J. Miquel Jordá-Gregori,a   Angeles Alvarez-Sorolla,a   José Sepúlveda-Arques,*b   Mario Orenac  and  Roberta Galeazzi*c  

* Corresponding authors

a University of Valencia, Avda. Vicent Andrés Estelles s/n, Valencia, 46100 Burjassot, Spain
E-mail: jose.sepulveda@uv.es
Fax: +34 96 386493
Tel: +34 96 3864938

b Department of Chemistry, University Cardenal Herrera-CEU, Edificio Seminario s/n, Valencia, 46133 Moncada, Spain
E-mail: eugenia@uch.ceu.es
Fax: +34 96 1395272
Tel: +34 96 1369000

c Dipartimento di Scienze dei Materiali e della Terra, University of Ancona, Via Brecce Bianche, I-60131 Ancona, Italy
E-mail: roberta@popcsi.unian.it
Fax: +39 71 2204714
Tel: +39 71 2204707

Abstract

threo-N-Alkoxycarbonylamino epoxides 5a–d, containing the oxazolidine moiety, were converted into trans-4,5-disubstituted-2-oxazolidin-2-ones 2 with total regio- and stereoselection by means of nucleophilic intramolecular attack of the carbamate moiety to the protonated oxirane ring. Theoretical calculations confirmed both the regioselection and the preference of the cyclocarbamation reaction vs. the intermolecular attack by the solvent, arising from different behaviour in comparison with the analogous iodonium ions.

Graphical abstract: Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides: a computational study

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Article information

DOI
https://doi.org/10.1039/B203702E
Article type
Paper
Submitted
17 Apr 2002
Accepted
30 May 2002
First published
24 Jun 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1650-1654

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Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides: a computational study

F. J. Casado-Bellver, M. E. González-Rosende, A. Asensio, J. M. Jordá-Gregori, A. Alvarez-Sorolla, J. Sepúlveda-Arques, M. Orena and R. Galeazzi, J. Chem. Soc., Perkin Trans. 1, 2002, 1650 DOI: 10.1039/B203702E

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