Hydrogen bonding aromatic oximes

During hydrogenation, intermediate aromatic hydroxylamines may undergo various cyclization reactions in molecules containing a suitably disposed carbonyl group, or carbonyl derivative, such as an oxime (13). The cyclized product may or may not maintain the N—OH bond, depending on the solvent, the catalyst, and the electrophilicity of the carbonyl (27,28,29,32,67,68). 

The scope of chiral recognition on these hydrogen bonding phases (mainly on diamides) has recently been shown to extend also to alcohols in the form of their carbamates, and to ketones derivatized to their oximes [12]. Furthermore, selectands which do not contain nitrogen, such as some free alcohols [10], a-hydroxy esters [11], perfluorinated acyl derivatives of sugars [13] and aromatic diols, have also been resolved on diamides. 

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