The Diels-Alder reaction is considered one of the most useful and fundamentally important reactions in organic chemistry because it has the power to construct two new carbon-carbon bonds in one step producing a six-membered ring. Utilizing alkynyl ketones (ynones) in a Lewis acid catalyzed Diels-Alder reaction produces chemically useful 1,4-cyclohexadiene products. We proposed that the <i>α,β</i>-unsaturated alkene intermediate could undergo a second Diels-Alder reaction in the presence of excess diene or the introduction of a second diene. The proposed bicyclic product formed from this tandem Diels-Alder is a <i>cis</i>-decalin, which is an important structural motif found in terpenoid natural products. The details of a tandem Diels-Alder to form four new carbon-carbon bonds in a one-pot reaction and substrate scope are presented.

Efficient synthesis of bicylco[4.4.0]decanes by tandem Diels-Alder of activated alkynes

253rd National Meeting (2017)

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