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

F. Javier Casado-Bellver, M. Eugenia González-Rosende, Amparo Asensio, J. Miquel Jordá-Gregori, Angeles Alvarez-Sorolla, José Sepúlveda-Arques, Mario Orena, Roberta Galeazzi

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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.

Original languageEnglish
Pages (from-to)1650-1654
Number of pages5
JournalJournal of the Chemical Society. Perkin Transactions 1
Issue number14
Publication statusPublished - 2002

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ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Casado-Bellver, F. J., González-Rosende, M. E., Asensio, A., Jordá-Gregori, J. M., Alvarez-Sorolla, A., Sepúlveda-Arques, J., Orena, M., & Galeazzi, R. (2002). Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides: A computational study. Journal of the Chemical Society. Perkin Transactions 1, (14), 1650-1654.