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Synthesis 1992; 1992(11): 1170-1178
DOI: 10.1055/s-1992-26328
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Herstellung enantiomerenreiner Sulfoxide aus Milchsäure und 3-Hydroxybuttersäure: Isopropenyl-tolyl-sulfoxid und 2-(Phenylsulfinyl) acrylester

Richard Breitschuh* , Dieter Seebach
  • *Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstraße 16, CH-8092 Zürich, Switzerland
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Publikationsdatum:
17. September 2002 (online)

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Preparation of Enantiomerically Pure Sulfoxides from Lactic Acid and 3- Hydroxybutyric Acid. Isopropenyl Tolyl Sulfoxide and 2-(Phenylsulfinyl) acrylate The EPC-synthesis of sulfoxides from readily available starting materials ("chiral pool") is demonstrated for the first time. Cyclic and open-chain thioethers derived from lactic and 3-hydroxybutyric acid are oxidized to sulfoxides, and the resulting products isolated in diastereomerically and enantiomerically pure form. Simple, large-scale conversions lead to methyl (S)-2-(phenylsulfinyl)acrylate and to (R)-isopropenyl tolyl sulfoxide from the corresponding (S)-lactate. Oxidation with tert-butyl hydroperoxide of chiral P-tolylthio-substituted propanols and butanols catalyzed by the addition of 1 % bis(2,4-pentadione)oxyvanadium(IV) (VOacac2) is diastereoselective (2:1 to 5.5: 1).