Journal of the American Chemical Society, Vol.132, No.22, 7598-7598, 2010
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.