Research in our laboratory has demonstrated the efficient preparation of oxepanes, 7-membered oxygen-containing rings, by cyclopropane fragmentation, a method that constructs a new bond by utilizing the significant strain energy contained in cyclopropanes. An analogous strategy has been applied to nitrogenous heterocycles such as piperidines and azepines, which comprise the backbone of many medicinally significant structures. The formation of the heterocycle can be accomplished by preparing a cyclic aminal, activating it to form an iminium species, and cyclizing using a cyclopropanol unit prepared by the Kulinkovich reaction.

Synthesis of nitrogenous heterocycles via cyclopropane fragmentation

246th National Meeting (2013)

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