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Synlett 1990; 1990(2): 99-102
DOI: 10.1055/s-1990-21000
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Synthesis of Enantiomerically Pure 2,4-trans-Substituted 3-Arenesulfonyl-1,3-oxazolidines by Lewis Acid Mediated Substitution of the 2-Methoxy Derivatives and their Epimerization

Kilian Conde-Frieboes* , Dieter Hoppe
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstrasse 40-60, D-2300 Kiel 1, Federal Republic of Germany
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Publication Date:
08 March 2002 (online)

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2-Methoxy-3-(p-toluenesulfonyl)-1,3-oxazolidines, derived from enantiomerically pure ß-hydroxyamines, condense with allyltrimethylsilane or trimethylsilyl enol ethers in the presence of trimethylsilyl triflate or zinc chloride etherate to yield the 2-(2-propenyl) or 2-(2-oxoalkyl) derivatives, respectively. The unknown 2,4-trans-diastereomers, formed in several examples predominantly, can be epimerized completely to give the 2,4-cis-oxazolidines.