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Synlett 2000; 2000(6): 0893-0895
DOI: 10.1055/s-2000-6699
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Stereocontrolled Ring Enlargement by Diastereoselective Stevens Rearrangement in Chiral 1,3-Oxazolidinium Salts. A Novel Entry to Enantiopure Morpholines

Rafael Pedrosa* , Celia Andrés, Manuel Delgado
  • *Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Valladolid, Dr. Mergelina s/n, 47011-Valladolid, Spain; Fax +983-423013; E-mail: pedrosa@qo.uva.es
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Publication Date:
31 December 2000 (online)

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Chiral oxazolidinium salts were prepared by treatment of (-)-ephedrine derived oxazolidines with allylic bromides. These quaternary salts undergo regio- and diastereoselective Stevens rearrangement by treatment with sodium hydride. The reaction constitutes a novel entry to enantiopure tetrasubstituted morpholines.

asymmetric synthesis - Stevens rearrangement - chiral ylides - chiral morpholines - chiral oxazolidines