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Synthesis 1992; 1992(10): 947-949
DOI: 10.1055/s-1992-26273
short paper
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(S)-3-Aminothiolane: A New Chiral Building Block

Eckehard Volker Dehmlow* , Ralf Westerheide
  • *Fakultät für Chemie, Universität Bielefeld, D-4800 Bielefeld, Germany
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Publication Date:
17 September 2002 (online)

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Methioninol [2-amino-4-(methylthio)butan-1-ol] is converted into (S)-4, 5-dihydro-4-[2-(methylthio)ethyl]-2-phenyl-1,3-oxazole (1). An acid-catalyzed rearrangement of 1 gives (S)-(-)-3- (benzoylamino)tetrahydrothiophene (2) in a stereospecific fashion. The transformation of the title compound 3 into the respective 3-hydroxytetrahydrothiophene proceeds only under partial inversion.