It has previously been shown that oxidative functionalization of allenes can produce synthetic motifs containing three contiguous, stereoselective carbon-heteroatom bonds, owing to the axial to point chirality and the three adjacent reactive sites. Here, allene-containing macrocycles, formed by the intramolecular N-H insertion of a sulfamate into the diazo compound, are used as another way to access these highly functionalized motifs. A range of potential ring sizes were studied, as well as the various heteroatom functionalities that can be used to form the macrocycle. From intramolecular attack on the allene, bicyclic heterocycles of varying sizes with functionalization at all three allene carbons can be obtained.

Formation and further reactivity of allene-containing macrocycles

245th National Meeting (2013)

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