New routes to oxazoles, thiazoles, and imidazoles continue to be of interest to the synthetic community, as these moieties are common in pharmacologically active compounds and natural products. In the course of our studies on reactive heterocyclic intermediates, we discovered a direct approach to these heterocycles. Here we report a one pot procedure to heterocycles of type (2) from readily available allenes (1). Experimental and computational data support intramolecular general acid catalyzed spirodiepoxide opening.
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Back to The 37th Middle Atlantic Regional Meeting (May 22-25, 2005)