Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by <i>H</i>-Phosphonates: Construction of Phosphinylindane Derivatives

Abstract

A highly regioselective divergent approach for the phosphine-containing indane/indene derivatives from the ene-yne-oxazolone precursors was reported. An insight into the reaction mechanism involving the phospha-1,4-addition followed by 5-<i>exo-dig</i> ring closure with a concomitant C-P/C-C bond formation was also proposed. This promising protocol utilized <i>H</i>-phosphonate as the phosphonating reagent in a silver-catalyzed or base-mediated cascade cyclization to construct the corresponding phosphorylated spiroindenoxazolones and amidoindenes, respectively, in good yields (up to 88% yield).