Reactivity N-Own: Pyridine N-oxides can be used for the complete regio- and stereoselective synthesis of trans-substituted piperidines. The sequential addition of Grignard reagents and aldehydes or ketones to pyridine N-oxides yields a complete regio- and stereoselective trans 2,3-addition reaction in high yields, and the substituted 2,3-dihydropyridine N-oxide can be reduced to form 2,3-trans-substituted piperidines (see scheme).
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Andersson et al. (2009) studied this question.