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Synthesis 1991; 1991(12): 1157-1162
DOI: 10.1055/s-1991-28410
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Diastereoselective Synthesis of Enantiomerically Pure 3-Organosulfonyl-2-(2-oxocycloalkyl)-1,3-oxazolidines from 2-Formylcycloalkanones and ß-Aminoalkanols

Inga Hoppe* , Holger Hoffmann, Ingeborg Gärtner, Thomas Krettek, Dieter Hoppe
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstr. 40, D-2300 Kiel, Germany
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Publication Date:
29 April 2002 (online)

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The title compounds (3-arylsulfonyl- or 3-mesyl-2-(2-oxocycloalkyl)-1, 3-oxazolidines) belonging to two different diastereomeric series, are prepared selectively by variation of the condensation conditions. By this, the chiral information of the 2-amino- 1-alkanol is extended to the cycloalkanone ring. Opposite configuration can be set up at the stereogenic center adjacent to the carbonyl group by using the same chiral auxiliary.