A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available b-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 b-hydroxyalkyl phenyl selenides as starting materials

Ring Closure Reactions by 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.

TIECCO, Marcello;TESTAFERRI, Lorenzo;TEMPERINI, Andrea;BAGNOLI, Luana;MARINI, Francesca;SANTI, Claudio
2004

Abstract

A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available b-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 b-hydroxyalkyl phenyl selenides as starting materials
2004
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11391/152119
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