TY - JOUR
T1 - Stereoselective synthesis of trans-4,5-disubstituted oxazolidin-2-ones by intramolecular conjugate addition of N-p-toluenesulfonyl carbamates
AU - Ciclosi, Marco
AU - Fava, Cristiana
AU - Galeazzi, Roberta
AU - Orena, Mario
AU - Sepúlveda-Arques, José
AU - González-Rosende, Maria Eugenia
PY - 2003/5/1
Y1 - 2003/5/1
N2 - 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.
AB - 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.
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M3 - Article
AN - SCOPUS:0037696433
VL - 60
SP - 1173
EP - 1183
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 5
ER -