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Synlett 1996; 1996(4): 289-296
DOI: 10.1055/s-1996-5400
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Asymmetric Pummerer-Type Reactions Induced by O-Silylated Ketene Acetals

Yasuyuki Kita* , Norio Shibata
  • *Faculty of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka 565, Japan
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Publikationsdatum:
31. Dezember 2000 (online)

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O-Silylated ketene acetals are effective reagents for the asymmetric Pummerer-type rearrangement and the asymmetric intramolecular Pummerer-type cyclization of chiral, non-racemic sulfoxides. The reactions proceed smoothly in the presence or absence of a catalytic amount of zinc iodide or zinc chloride in acetonitrile, tetrahydrofuran or dichloromethane. These Pummerer-type reactions show the highest optical induction of all previously examined methods. Moreover, the reaction can be applied to an asymmetric synthesis of β-lactam antibiotics.

O-silylated ketene acetal - Pummerer reaction - asymmetric - penicillin biosynthesis - chiral sulfoxide