Abstract
The development and utilization of highly functionalized and reactive dienophiles in the Diels–Alder cyclization reaction is of value in producing diversely functionalized, and therefore useful, cyclic products. We have developed a Diels–Alder reaction of conjugated 2,4-diynones, promoted by Lewis acids, to produce substituted 2-alkynyl-1,4-cyclohexadiene (‘skipped’ cyclohexadiene) products in good to excellent yields. The reaction was successful with a variety of cyclic and acyclic dienes as well as with a diversity of 2,4-diynones.
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