Diastereoselective oxidative α-amination of aliphatic aldehydes catalyzed by iodine: synthesis of syn-γ-hydroxy-α-amino acetals

Aldehydes can react with secondary amines to give alpha-amino acetals via the alpha-amination of aliphatic aldehydes catalyzed by iodine. The presence of an asymmetric hydroxylated center at the gamma-position of the aldehyde was found to induce the stereoselective amino group. This method represents a stereoselective alpha-amination of gamma-hydroxyaldehydes for the synthesis of syn-gamma-hydroxy-alpha-amino acetals in good yields and reasonable diastereoselectivities under very mild conditions.