The direct and enantioselective organocatalytic alpha-oxidation of aldehydes.
J Am Chem Soc
; 125(36): 10808-9, 2003 Sep 10.
Article
in En
| MEDLINE
| ID: mdl-12952459
ABSTRACT
The first direct enantioselective catalytic alpha-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 alpha-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.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Proline
/
Aldehydes
Language:
En
Journal:
J Am Chem Soc
Year:
2003
Type:
Article
Affiliation country:
United States