Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by H‑Phosphonates: Construction of Phosphinylindane Derivatives

Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by H‑Phosphonates: Construction of Phosphinylindane Derivatives

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...

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Veröffentlicht in:Journal of organic chemistry 2021-07, Vol.86 (14), p.9360-9383
Hauptverfasser: Worayuthakarn, Rattana, Deesiri, Sirikan, Chainok, Kittipong, Wannarit, Nanthawat, Ruchirawat, Somsak, Thasana, Nopporn
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container_end_page 9383
container_issue 14
container_start_page 9360
container_title Journal of organic chemistry
container_volume 86
creator Worayuthakarn, Rattana
Deesiri, Sirikan
Chainok, Kittipong
Wannarit, Nanthawat
Ruchirawat, Somsak
Thasana, Nopporn
description 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).
doi_str_mv 10.1021/acs.joc.1c00609
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title Highly Regioselective Tandem Reaction of Ene-Yne-Oxazolones Induced by H‑Phosphonates: Construction of Phosphinylindane Derivatives
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