Ru-Catalyzed Redox-Neutral Cleavage of the N–O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3 + 2]-Cycloaddition/N–O Cleavage

Ru-Catalyzed Redox-Neutral Cleavage of the N–O Bond in Isoxazolidines: Isatogens to Pseudoindoxyls via a One-Pot [3 + 2]-Cycloaddition/N–O Cleavage

A novel metal-catalyzed oxygen atom transfer reaction onto olefins is reported. By taking isatogens as substrates, a one-pot [3 + 2]-cycloaddition of nitrone with olefins followed by the Ru-catalyzed redox-neutral N–O bond cleavage of intermediate isoxazolidine has been executed as a simple method f...

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Veröffentlicht in:Organic letters 2015-06, Vol.17 (12), p.2870-2873
Hauptverfasser: Suneel Kumar, Chepuri V, Ramana, Chepuri V
Format: Artikel
Sprache:eng
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Zusammenfassung:A novel metal-catalyzed oxygen atom transfer reaction onto olefins is reported. By taking isatogens as substrates, a one-pot [3 + 2]-cycloaddition of nitrone with olefins followed by the Ru-catalyzed redox-neutral N–O bond cleavage of intermediate isoxazolidine has been executed as a simple method for the synthesis of 2,2-disubstituted pseudoindoxyls.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00837