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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 β‐Hydroxyalkyl Phenyl Selenides
Author(s) -
Tiecco Marcello,
Testaferri Lorenzo,
Temperini Andrea,
Bagnoli Luana,
Marini Francesca,
Santi Claudio
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305497
Subject(s) - tosyl , nucleophile , stereospecificity , intramolecular force , chemistry , ring (chemistry) , closure (psychology) , nitrogen , medicinal chemistry , group (periodic table) , stereochemistry , organic chemistry , catalysis , economics , market economy
A new and convenient method for the stereospecific synthesis of variously substituted 1,3‐oxazolidin‐2‐ones from the easily available β‐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 β‐hydroxyalkyl phenyl selenides as starting materials.