title: Electrochemical deallylation of alpha-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids.
abstract: Electrochemical oxidation of alpha-allylated and alpha-benzylated N-acylated cyclic amines by using a graphite anode easily affords the corresponding alpha-methoxylated products with up to 76 % yield. Ease of oxidation was affected by the type of electrode, the size of cyclic amine, and the nature of the protecting group. This method was successfully applied to the synthesis of optically active N-acylated alpha-alkyl-alpha-amino acid esters with up to 99 % ee.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
authors.forename: Peter G
authors.initials: PG
authors.lastname: Kirira
authors.forename: Masami
authors.initials: M
authors.lastname: Kuriyama
authors.forename: Osamu
authors.initials: O
authors.lastname: Onomura
mesh_terms: D000478:Alkylation; D000596:Amino Acids / Q000737:chemistry*; D004563:Electrochemistry; D004566:Electrodes; D006108:Graphite / Q000737:chemistry*; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010984:Platinum / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D010984:Platinum; D006108:Graphite