title: Highly enhanced enantioselectivity in the memory of chirality via acyliminium ions.
abstract: [reaction: see text] Electrochemical oxidation of N-acylated serine derivative 1b in methanol gave optically active methoxylated compound 2b with an enantiomeric excess of up to 80%. The bulky o-phenyl benzoyl N-protecting group was found to be the main contributing factor for the enhanced enantioselectivity. The mechanistic aspect of this methoxylation reaction was investigated and found to proceed via a retention mechanism.
authors.affiliation: Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki City, Nagasaki 852-8521, Japan.
authors.forename: G Ng'ang'a
authors.initials: GN
authors.lastname: Wanyoike
authors.forename: Osamu
authors.initials: O
authors.lastname: Onomura
authors.forename: Toshihide
authors.initials: T
authors.lastname: Maki
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Matsumura