Highly enhanced enantioselectivity in the memory of chirality via acyliminium ions.
[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.
Wanyoike
G Ng'ang'a
GN
Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki City, Nagasaki 852-8521, Japan.
Onomura
Osamu
O
Maki
Toshihide
T
Matsumura
Yoshihiro
Y