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Highly Enhanced Enantioselectivity in the Memory of Chirality via Acyliminium Ions

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journal contribution
posted on 2002-04-30, 00:00 authored by G. Ng'ang'a Wanyoik, Osamu Onomura, Toshihide Maki, Yoshihiro Matsumura
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.

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