Highly enhanced enantioselectivity in the memory of chirality via acyliminium ions

G Ng'ang'a Wanyoike; Osamu Onomura; Toshihide Maki; Yoshihiro Matsumura

doi:10.1021/ol025865r

Highly enhanced enantioselectivity in the memory of chirality via acyliminium ions

Org Lett. 2002 May 30;4(11):1875-7. doi: 10.1021/ol025865r.

Authors

G Ng'ang'a Wanyoike¹, Osamu Onomura, Toshihide Maki, Yoshihiro Matsumura

Affiliation

¹ Department of Pharmaceutical Sciences, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki City, Nagasaki 852-8521, Japan.

PMID: 12027636
DOI: 10.1021/ol025865r

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.