Stereoselective synthesis of trans-4,5-disubstituted oxazolidin-2-ones by intramolecular conjugate addition of N-p-toluenesulfonyl carbamates

Marco Ciclosi, Cristiana Fava, Roberta Galeazzi, Mario Orena, José Sepúlveda-Arques, Maria Eugenia González-Rosende

Research output: Contribution to journalArticle

Abstract

p-Toluenesulfonyl carbamates (2a-d) were prepared starting from allylic alcohols (3), in which the double bond is conjugated with an electron withdrawing group. In the presence of a catalytic amount of DBU, an intramolecular cyclisation occurred, leading to trans-4,5-disubstituted oxazolidin-2-ones (1a-d) with total stereoselection, which can be precursors of syn-4-hydroxy-3-amino acids.

Original languageEnglish
Pages (from-to)1173-1183
Number of pages11
JournalHeterocycles
Volume60
Issue number5
Publication statusPublished - May 1 2003

ASJC Scopus subject areas

  • Organic Chemistry

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    Ciclosi, M., Fava, C., Galeazzi, R., Orena, M., Sepúlveda-Arques, J., & González-Rosende, M. E. (2003). Stereoselective synthesis of trans-4,5-disubstituted oxazolidin-2-ones by intramolecular conjugate addition of N-p-toluenesulfonyl carbamates. Heterocycles, 60(5), 1173-1183.