α‑Aminoxylation of Ketones and β‑Chloro-α-aminoxylation of Enones with TEMPO and Chlorocatecholborane

α‑Aminoxylation of Ketones and β‑Chloro-α-aminoxylation of Enones with TEMPO and Chlorocatecholborane

Oxidation of various cyclic and acyclic ketones under mild conditions with chlorocatecholborane, a bulky pyridine base, and TEMPO to the corresponding α-aminoxylated products in good to excellent yields (52–99%) is described. For enones as substrates, products of a β-chloro-α-aminoxylation are obtai...

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Veröffentlicht in:Organic letters 2012-09, Vol.14 (17), p.4474-4477
Hauptverfasser: Li, Yi, Pouliot, Martin, Vogler, Thomas, Renaud, Philippe, Studer, Armido
Format: Artikel
Sprache:eng
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Zusammenfassung:Oxidation of various cyclic and acyclic ketones under mild conditions with chlorocatecholborane, a bulky pyridine base, and TEMPO to the corresponding α-aminoxylated products in good to excellent yields (52–99%) is described. For enones as substrates, products of a β-chloro-α-aminoxylation are obtained (70–89%).
ISSN:1523-7060
1523-7052
DOI:10.1021/ol301979b