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Allylic Chloro-Tetrahydropyridines: Kinetic Resolutions and Stereospecific Reactions of Enantiomerically Enriched Allyl Chlorides

We report
the kinetic resolution of racemic allyl
chlorides via a copper-catalysed asymmetric allylic alkylation. Novel 3-alkyl substituted tetrahydropyridines and enantioenriched 3-chloro-1,2,3,6-tetrahydropyridines are
formed in high enantioselectivities. The piperidine-based allyl halides undergo highly enantiospecific
substitution reactions with C, N, O and S-based nucleophiles. Experiments with
deuterium-labelled chloro-tetrahydropyridine and DFT calculations were used to
investigate the mechanistic pathways of the reactions.