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Synlett 1996; 1996(2): 182-184
DOI: 10.1055/s-1996-5339
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1,2-Additions of Silylenol Ethers to 4-Silyloxy-1-benzothiopyrylium Triflates: A New and Efficient Method for the Synthesis of 2-Substituted Benzothiopyran-4-ones

Uwe Beifuss* , Mario Tietze, Henning Gehm
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Göttingen, Germany, Fax +49(551)39-9660
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Publikationsdatum:
31. Dezember 2000 (online)

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The regioselective 1,2-addition of silylenol ethers to the C=S+-bond of 4-silyloxy-1-benzothiopyrylium triflates yields the corresponding bis-silylenol ethers which can be hydrolyzed selectively to give the respective ketosilylenol ether or 1,5-diketones. The new method is an equivalent to the 1,4-addition of nucleophiles to β-thio-α,β-unsaturated cyclic ketones.

1-Benzothiopyrylium Triflates - Silylenol Ether - 1,2-Addition - 1,4-Addition - S-Heterocycles