title: Diastereoselective oxidative α-amination of aliphatic aldehydes catalyzed by iodine: synthesis of syn-γ-hydroxy-α-amino acetals.
abstract: Aldehydes can react with secondary amines to give α-amino acetals via the α-amination of aliphatic aldehydes catalyzed by iodine. The presence of an asymmetric hydroxylated center at the γ-position of the aldehyde was found to induce the stereoselective amino group. This method represents a stereoselective α-amination of γ-hydroxyaldehydes for the synthesis of syn-γ-hydroxy-α-amino acetals in good yields and reasonable diastereoselectivities under very mild conditions.
authors.affiliation: School of Chemistry and molecular Engineering, Zhengzhou University, Zhengzhou 450052, P.R. China.
authors.forename: Yun-Xiao
authors.initials: YX
authors.lastname: Zhang
authors.forename: An-Qi
authors.initials: AQ
authors.lastname: Zhang
authors.forename: Jie-Sheng
authors.initials: JS
authors.lastname: Tian
authors.forename: Teck-Peng
authors.initials: TP
authors.lastname: Loh
mesh_terms: D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000447:Aldehydes; D000588:Amines; D007455:Iodine