Vinylphosphonium Salt-Mediated Reactions: A One-Pot Condensation Approach for the Highly cis-Selective Synthesis of N-Benzoylaziridines and the Green Synthesis of 1,4,2-Dioxazoles as Two Important Classes of Heterocyclic Compounds.

An efficient, one-pot, and convenient approach for the reaction of the same precursors, trialkyl(aryl) phosphines, acetylene diesters, and benzhydroxamic acids has been developed to produce two important classes of heterocyclic compounds: N-benzoylaziridines and 1,4,2-dioxazoles. The strategy utilizes the intermediate solvation as a key step in product selectivity. The usefulness of the developed approach has been confirmed in the unprecedented highly cis-selective formation of the N-benzoylaziridines. In addition, the procedure provides a green alternative method for the synthesis of 1,4,2-dioxazoles employing a β-cyclodextrin nanoreactor in aqueous media.