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Synthesis 1997; 1997(4): 450-454
DOI: 10.1055/s-1997-1198
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Preparation of 2-Oxazolidinones by Intramolecular Nucleophilic Substitution

Floris L. van Delft, Cornelis M. Timmers, Gijs A. van der Marel, Jacques H. van Boom*
  • *Gorlaeus Laboratories, Leiden Institute of Chemistry, P.O.Box 9502, 2300 RA, Leiden, The Netherlands, Fax +31(71)5274307; E-mail j.boom@chem.LeidenUniv.nl
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Publication History

Publication Date:
31 December 2000 (online)

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Treatment of N-alkoxycarbonyl, N-benzyl protected β-amino alcohols with triphenylphosphine and hexachloroethane in 1,2-dichloroethane induces cyclization to 2-oxazolidinones, which are found by intramolecular attack with inversion of configuration at the secondary alcohol. In contrast, mono N-substituted alkyl carbamates undergo chlorination under the same conditions.

β-amino alcohols - 2-oxazolidinones - cyclocarbamation - inversion - chlorination