Journal of the Chinese Chemical Society p. 83 - 90 (2000)
Update date:2022-08-02
Topics:
Chou, Shang-Shing P.
Liang, Pi-Wei
The title compound 2 was readily prepared by MCPBA oxidation of the sulfide 1. Thermal desulfonylation of 2 gave the sulfoxide-substituted diene 3. The Diels-Alder reactions of 3 with various dienophiles gave the cyclized products 4-9 in good yields. The regiochemistry was found to be dominated by the phenylsulfinyl group, but could be reversed by the presence of a Lewis acid. Deprotonation of 2 by BuLi, followed by the reaction with alkyl halides, gave the substituted 2-sulfolenes 10. A synthetic application of 10 was demonstrated by converting 10e to the bicyclic product 11.
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