Asymmetric oxidation of verbenone ethylene dithioacetal |
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| Authors: | A V Timshina S A Rubtsova L L Frolova I N Alekseev P A Slepukhin A V Kuchin |
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| Institution: | (1) Institute of Chemistry, Komi Research Center, Ural Division, Russian Academy of Sciences, ul. Pervomaiskaya 48, Syktyvkar, 167982, Russia;(2) Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi 20, Yekaterinburg, 620219, Russia |
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| Abstract: | Asymmetric oxidation of verbenone ethylene dithioacetal with m-chloroperoxybenzoic acid at different substrate-to-oxidant ratios in methylene chloride at ?10°C gave previously unknown (1S,1′S,2S,3′S,5S)-4,6,6-trimethylspirobicyclo3.1.1]hept-3-ene-2,2′-1,3]dithiolane] 1′,3′-dioxide, (1S,2S,3′S,5S)-4,6,6-trimethylspirobicyclo3.1.1]hept-3-ene-2,2′-1,3]dithiolane] 1′,1′,3′-trioxide, and (1S,5S)-4,6,6-trimethylspirobicyclo-3.1.1]hept-3-ene-2,2′-1,3]dithiolane] 1′,1′,3′,3′-tetraoxide whose structure was determined by X-ray analysis. |
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