6533b838fe1ef96bd12a3b45
RESEARCH PRODUCT
Synthesis of chiral oxazolidin-2-ones from N-alkoxycarbonyl amino epoxides: a computational studyElectronic supplementary information (ESI) available: structures of localized transition states. See http://www.rsc.org/suppdata/p1/b2/b203702e/
Amparo AsensioAngeles Alvarez-sorollaJosé Sepúlveda-arquesM. Eugenia González-rosendeJ. Miquel Jorda-gregoriRoberta GaleazziMario OrenaF. Javier Casado-bellversubject
SolventOxazolidinechemistry.chemical_compoundNucleophileChemistryStereochemistryIntramolecular forceIntermolecular forceMoietyProtonationRing (chemistry)description
threo-N-Alkoxycarbonylamino epoxides 5a–d, containing the oxazolidine moiety, were converted into trans-4,5-disubstituted-2-oxazolidin-2-ones 2 with total regio- and stereoselection by means of nucleophilic intramolecular attack of the carbamate moiety to the protonated oxirane ring. Theoretical calculations confirmed both the regioselection and the preference of the cyclocarbamation reaction vs. the intermolecular attack by the solvent, arising from different behaviour in comparison with the analogous iodonium ions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-06-24 | Journal of the Chemical Society, Perkin Transactions 1 |