Enantiomerically Enriched Tetrahydropyridine Allyl Chlorides

27 November 2019, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Enantiomerically enriched allyl halides are rare due to their configurational lability. Here we report stable piperidine-based allyl chloride enantiomers. These allyl chlorides can be produced via resolution, and undergo highly enantiospecific catalyst-free substitution reactions with C, N, O and S-based nucleophiles. Deuterium-labelled chloro-tetrahydropyridine, selectively prepared using the H/D primary kinetic isotope effect, and DFT calculations were used to investigate the mechanisms of the reactions. The allyl chlorides may also serve as valuable mechanistic tools for probing stereoselective reaction pathways.


Kinetic Resolution
copper catalysis
Asymmetric Allylic Alkylation
stereospecific reaction
deuterium labelling

Supplementary materials

ESI Allyl Chlorides


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