Details

Autor(en) / Beteiligte

• Brown, Sean P
• Brochu, Michael P
• Sinz, Christopher J
• MacMillan, David W. C

Titel

The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes

Ist Teil von

• Journal of the American Chemical Society, 2003-09, Vol.125 (36), p.10808-10809

Ort / Verlag

Washington, DC: American Chemical Society

Erscheinungsjahr

2003

Quelle

MEDLINE

Beschreibungen/Notizen

• The first direct enantioselective catalytic α-oxidation of carbonyls has been accomplished. The use of enamine catalysis has provided a new organocatalytic strategy for the enantioselective oxyamination of aldehydes, to generate α-oxyaldehydes, important chiral synthons for natural product and medicinal agent synthesis. The use of l-proline as the asymmetric catalyst has been found to mediate the oxidation of a large variety of aldehyde substrates with nitrosobenzene serving as the electrophilic oxidant. A diverse spectrum of aldehyde substrates can also be accommodated in this new organocatalytic transformation. While catalyst quantities of 2 mol % were generally employed in this study, successful oxidations conducted using catalyst loadings as low as 0.5 mol % are described.