6533b7d0fe1ef96bd125b77a
RESEARCH PRODUCT
Stereoselective Synthesis of trans-4,5-Disubstituted Oxazolidin-2-ones by Intramolecular Conjugate Addition of N-p-Toluenesulfonyl Carbamates.
Mario OrenaCristiana FavaRoberta GaleazziMarco CiclosiMaria Eugenia González-rosendeJosé Sepúlveda-arquessubject
Pharmacologychemistry.chemical_classificationAllylic rearrangementDouble bondStereochemistryChemistryOrganic Chemistryfood and beveragesGeneral MedicineConjugated systemMedicinal chemistryAnalytical ChemistryCatalysisIntramolecular forcePolar effectStereoselectivityConjugatedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-09-02 | ChemInform |