Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by H-Phosphonates: Construction of Phosphinylindane Derivatives
2021
Worayuthakarn, Rattana | Deesiri, Sirikan | Chainok, Kittipong | Wannarit, Nanthawat | Ruchirawat, Somsak | Thasana, Nopporn
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-exo-dig ring closure with a concomitant C–P/C–C bond formation was also proposed. This promising protocol utilized H-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).
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