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First Example of Memory of Chirality in Carbenium Ion Chemistry

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journal contribution
posted on 17.05.2000 by Yoshihiro Matsumura, Yuki Shirakawa, Yuki Satoh, Meri Umino, Takayoshi Tanaka, Toshihide Maki, Osamu Onomura
The non-Kolbe reaction of N-benzoyloxazolidine derivatives 6 derived from l-serine gave optically active N,O-acetals 7 when graphite was used as an anode material. This reaction represents the first example of “memory of chirality” in carbenium ion chemistry. The material used for the anode was critical for the memory of chirality. The substitution of carboxyl group with methoxyl group was found to proceed with an inversion mechanism.