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

28 May 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Kinetic Resolution
copper catalysis
Asymmetric Allylic Alkylation
stereospecific reaction
deuterium labelling

Supplementary materials

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