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Enantiomerically Enriched Tetrahydropyridine Allyl Chlorides

preprint
revised on 18.11.2019, 09:00 and posted on 27.11.2019, 07:00 by Sedef Karabiyikoglu, Alexandre Brethomé, Thomas Palacin, Robert Paton, Stephen P. Fletcher
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.

History

Email Address of Submitting Author

alexandre.brethome@chem.ox.ac.uk

Institution

University of Oxford

Country

United Kingdom

ORCID For Submitting Author

0000-0002-0706-4344

Declaration of Conflict of Interest

Oxford University Innovation has filed a patent application (GB1815018.5) with S.P.F. and S.K named as inventors. The remaining authors declare no competing financial interests.

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