First example of memory of chirality in carbenium ion chemistry

[GRAPHICS] 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 an ode material, This reaction represents the first example of "memory of chir ality" in carbenium ion chemistry, The material used for the anode was crit ical for the memory of chirality, The substitution of carboxyl group with m ethoxyl group was found to proceed with an inversion mechanism.