Attempted asymmetric electrochemical reductions in magnetic fields

Because of negative, ambiguous or controversial results claimed by previous investigators studying the potential efficacy of magnetic fields in directing asymmetric syntheses and because of its potential importance as regards the origin of optical activity, we have attempted to confirm a recent report by Takahashiet al. (1986), who claimed that phenylglyoxylic acid (XIX) may be reduced electrochemically at a mercury cathode placed in a magnetic field of 0.168 T to optically active mandelic acid (XX), with optical yields favoring the S(+)-XX enantiomer as high as 25%. We have found that the complete reduction of XIX in pH 3.8 acetate buffer at a mercury cathode in magnetic fields of either 0.14 or 7.05 T leads only to racemic XX products. The earlier literature describing attempted absolute asymmetric syntheses in magnetic, electric and gravitational fields is briefly and critically reviewed.