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Communication | Special issue | Vol 79, No. 1, 2009, pp.339-345
Published online, 2nd October, 2008
DOI: 10.3987/COM-08-S(D)10
Memory of Chirality in the Electrochemical Oxidation of N-o-phenylbenzoylated Prolinols

George Ng’aNg’a Wanyoike, Yoshihiro Matsumura, and Osamu Onomura*

*Graduate School of Biomedical Sciences, Nagasaki University, 1-14, Bunkyo-machi, Nagasaki 852-8521, Japan

Abstract

Memory of chirality in electrochemical carbon-carbon bond cleavage of N-o-phenylbenzoylated (S)-prolinol derivatives was observed. Substituents of the α-position affected the ee of the products. The reaction of α,α-diarylated (S)-prolinol derivatives proceeded smoothly to afford optically active α-methoxylated pyrrolidine with up to 73% ee.