Ring-closure reactions through intramolecular displacement of the phenylselenonyl group by nitrogen nucleophiles: a new stereospecific synthesis of N-tosyl and N-benzoyl-1,3-oxazolidin-2-ones from beta-hydroxyalkyl phenyl selenides.
A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available beta-hydroxyalkyl phenyl selenides is presented. After transformation into the N-tosyl or N-benzoyl carbamates, the selenides were oxidized to the corresponding selenones. The key step of the process is the ring-closure reaction, which occurs by stereospecific intramolecular nucleophilic substitution of the selenone group by the nitrogen atom of the carbamate. Enantiomerically pure 1,3-oxazolidin-2-one derivatives can be easily prepared by using enantiomerically pure beta-hydroxyalkyl phenyl selenides as starting materials.
Tiecco
Marcello
M
Dipartimento di Chimica e Tecnologia del Farmaco, Sezione di Chimica Organica, Università di Perugia, 06123 Perugia, Italy. tiecco@unipg.it
Testaferri
Lorenzo
L
Temperini
Andrea
A
Bagnoli
Luana
L
Marini
Francesca
F
Santi
Claudio
C
D003500:Cyclization; D008968:Molecular Conformation; D009584:Nitrogen / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D016566:Organoselenium Compounds; D023303:Oxazolidinones; D009584:Nitrogen