6533b834fe1ef96bd129cb55
RESEARCH PRODUCT
Experimental and theoretical investigations for the regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones
José Sepúlveda-arquesElena Zaballos-garcíaLuis R. DomingoPau ArroyoLuisa M. TestaMohamed Akssirasubject
chemistry.chemical_classificationRegiochemistryStereochemistryOrganic ChemistryIodideStereoselective synthesisRegioselectivityBiochemistrychemistryAb initio quantum chemistry methodsYield (chemistry)Drug DiscoveryMolecular mechanismStereoselectivityCis–trans isomerismdescription
The regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones takes place in good yield. However, the cis configuration at C2 and C3 in monocyclic aziridines is a limiting factor for this transformation. Ab initio calculations show that while the ring-opening process assisted by iodide is regioselective, the subsequent ring-closure is responsible for the retention of the configuration at the trans oxazolidin-2-ones. The larger energy found for the ring-closure process for the cis aziridines accounts for the non-formation of the cis oxazolidin-2-ones.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-01-01 | Tetrahedron |