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Paper | Regular issue | Vol 60, No. 5, 2003, pp.1173-1183
Published online, 3rd March, 2003
DOI: 10.3987/COM-03-9724
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, and Maria Eugenia González-Rosende*

*Dipartimento di Scienze dei Materiali e della Terra, Università di Ancona, Via Brecce Bianche, I-60131 Ancona, Italy

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.