Norcamphor, oximes

Electrochemical reductions of camphor oxime (R = Me) and norcamphor oxime (R = H) at a mercury cathode proceed with a high degree of diastereoselectivity (equation 3) . The products are in fact of opposite stereochemistry to those formed in dissolving metal (sodium-ethanol) reductions of the oximes. 

Cathodic reduction of camphor and norcamphor oxime 144a appears to be cases where the stereochemistry is controlled by attack by the electrode from the least hindered side of the molecule ... 

As expected, in the heterogeneous catalytic hydrogenation of norcamphor (R = H)85 and camphor (R = CH, )86 87 oximes, the amines resulting from hydrogenation of the imine from the least hindered side are formed. 

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