Strained organic compounds have captivated the scientific community for over a century. Whereas strained cyclic alkynes have seen a renaissance in the synthetic community over the past few decades, the chemistry of a related class of intermediates, cyclic allenes, has remained underdeveloped. This presentation will describe our efforts to generate strained heterocyclic allenes under mild conditions, the trapping of the resultant allenes in various cycloadditions, as well as the observed regio- and diastereoselectivities. In addition, efforts to intercept enantioenriched heterocyclic allenes for the preparation of optically active cycloadducts bearing medicinally-privileged heterocycles will be discussed.

Harnessing the reactivity of strained heterocyclic allenes

2019 Spring National Meeting

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