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

Chemistry. 2004 Apr 2;10(7):1752-64. doi: 10.1002/chem.200305497.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Molecular Conformation
  • Nitrogen / chemistry*
  • Organoselenium Compounds* / chemical synthesis
  • Organoselenium Compounds* / chemistry
  • Oxazolidinones / chemical synthesis*
  • Stereoisomerism

Substances

  • Organoselenium Compounds
  • Oxazolidinones
  • Nitrogen