Highly enantioselective alpha-aminoxylation of aldehydes and ketones with a polymer-supported organocatalyst.
The first catalytic enantioselective alpha-aminoxylation of aldehydes and ketones using an insoluble, polymer-supported organocatalyst (1) derived from trans-4-hydroxyproline is reported (ee: 96-99%). Reaction rates in the aminoxylation of cyclic ketones with 1 are higher than those reported with l-proline. The insoluble nature of 1 simplifies workup conditions and allows catalyst recycling without an apparent decrease in enantioselectivity or yield.
Font
Daniel
D
Institute of Chemical Research of Catalonia, Av Països Catalans, 16, Tarragona, Spain, and Departament de Química Orgànica, Universitat de Barcelona, Barcelona, Spain.
Bastero
Amaia
A
Sayalero
Sonia
S
Jimeno
Ciril
C
Pericàs
Miquel A
MA
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003512:Cyclohexanones / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D011108:Polymers / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D003512:Cyclohexanones; D007659:Ketones; D011108:Polymers; C036468:cyclohexanone; D011392:Proline; D009584:Nitrogen; D010100:Oxygen