6533b86efe1ef96bd12cb328

RESEARCH PRODUCT

Experimental and DFT study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism

Elena ZaballosMiguel A. GonzálezEl Mestafa El HadramiAbdelkarim El MoncefRamón J. Zaragozá

subject

chemistry.chemical_classificationReaction mechanismKetoneIntramolecular reactionStereochemistryOrganic ChemistryDiastereomerBiochemistrylaw.inventionSN1 reactionchemistrylawIntramolecular forceDrug DiscoverySN2 reactionWalden inversion

description

Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and/or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical calculations and additional experimental assays.

yearjournalcountryeditionlanguage
2010-07-01Tetrahedron
https://doi.org/10.1016/j.tet.2010.04.097