The Diels-Alder reaction has provided the foundation for some of the most impressive achievements in the area of cyclohexene derivative synthesis. Among various categories of the Diels-Alder reaction, the tandem reaction provides additional diversity to the Diels-Alder adduct. Our laboratory has been interested in sulfinyl retro-ene reaction that can be performed in tandem with the Diels-Alder reaction as a new post-modification sequence and developed a protocol for the synthesis highly substituted cyclohexenes. We have designed, synthesized and used (tert-Butyl)dimethylsilyloxymethyl (TBSOM) substituted dienes as a new diene for the Diels-Alder reaction. Using this new diene, the Diels-Alder reaction has been performed in thermal or Lewis acid catalyzed reaction conditions. The Diels-Alder adduct then can be oxidized and treated with an acidic reagent, whereby a sulfinic acid group is generated and undergoes a retro-ene reaction to give a series of cyclohexene core obtained via the reductive transposition. The reaction described here represents significant expansion of the scope of the Diels-Alder reaction. The details of our studies will be shown in this poster.

Synthesis of highly substituted cyclohexenes via traceless Diels-Alder and sulfinyl retro-ene tandem reaction

246th National Meeting (2013)

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