Unusual reversal of enantioselectivity in the proline-mediated alpha-amination of aldehydes induced by tertiary amine additives.
An intriguing reversal in product enantioselectivity accompanied by a change in the kinetic profile is observed in the alpha-amination of aldehydes catalyzed by proline in the presence of organic bases. Implications for the prevailing stereochemical models for proline and related aminocatalytic transformations are discussed.
Blackmond
Donna G
DG
Department of Chemistry, Imperial College London SW7 2AZ, UK. blackmond@scripps.edu
Moran
Antonio
A
Hughes
Matthew
M
Armstrong
Alan
A
D000447:Aldehydes / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
D000447:Aldehydes; D000588:Amines; D011392:Proline