Enantiomerically enriched tetrahydropyridine allyl chlorides
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 kinetic resolution, and undergo highly enantiospecific catalyst-free substitution reactions with C, N,...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Royal Society of Chemistry
2020
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| Summary: | 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 kinetic resolution, and undergo highly enantiospecific catalyst-free substitution reactions with C, N, O and S-based nucleophiles. DFT calculations and experiments with deuterium-labelled chloro-tetrahydropyridine, selectively prepared using H/D primary kinetic isotope effect, were used to investigate the mechanisms of resolution and substitution reactions. The allyl chlorides may also serve as valuable mechanistic tools for probing stereoselective reaction pathways. |
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