title: Synthesis of alpha-amino acid precursors directly from aldehydes using masked acyl cyanide reagents and N,O-dialkylated hydroxylamines.
abstract: A synthetic methodology for the synthesis of alpha-amino acid precursors directly from the corresponding aldehydes using N,O-dialkylated hydroxylamines and masked acyl cyanide (MAC) reagents was developed. The one-pot reaction can be carried out under mild conditions and without a separate purification step of the imino species. The method was applied to the synthesis of optically pure (+)-4-methylphenylglycine and the derivatives by using an Abiko-Masamune's tricyclic 1,2-oxazolidine as the chiral auxiliary.
authors.affiliation: Division of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School of the University of Tokushima, 1-78, Sho-machi, Tokushima 770-8505, Japan. nem@ph.tokushima-u.ac.jp
authors.forename: Hisao
authors.initials: H
authors.lastname: Nemoto
authors.forename: Rujian
authors.initials: R
authors.lastname: Ma
authors.forename: Tomoyuki
authors.initials: T
authors.lastname: Kawamura
authors.forename: Masaki
authors.initials: M
authors.lastname: Kamiya
authors.forename: Masayuki
authors.initials: M
authors.lastname: Shibuya
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000478:Alkylation; D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D019811:Hydroxylamine / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013696:Temperature
chemical_list: D000097:Acetonitriles; D000447:Aldehydes; D000596:Amino Acids; D003486:Cyanides; D019811:Hydroxylamine; D009584:Nitrogen; D010100:Oxygen; C032159:acetonitrile