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 |
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Royal Society of Chemistry
2020
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| _version_ | 1826283802275610624 |
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| author | Karabiyikoglu, S Brethome, AV Palacin, T Paton, RS Fletcher, SP |
| author_facet | Karabiyikoglu, S Brethome, AV Palacin, T Paton, RS Fletcher, SP |
| author_sort | Karabiyikoglu, S |
| collection | OXFORD |
| description | 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. |
| first_indexed | 2024-03-07T01:04:20Z |
| format | Journal article |
| id | oxford-uuid:8aceb4dc-0b1a-40bc-9a41-c7636645fed9 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T01:04:20Z |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:8aceb4dc-0b1a-40bc-9a41-c7636645fed92022-03-26T22:33:58ZEnantiomerically enriched tetrahydropyridine allyl chloridesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:8aceb4dc-0b1a-40bc-9a41-c7636645fed9EnglishSymplectic ElementsRoyal Society of Chemistry2020Karabiyikoglu, SBrethome, AVPalacin, TPaton, RSFletcher, SPEnantiomerically 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. |
| spellingShingle | Karabiyikoglu, S Brethome, AV Palacin, T Paton, RS Fletcher, SP Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title | Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title_full | Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title_fullStr | Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title_full_unstemmed | Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title_short | Enantiomerically enriched tetrahydropyridine allyl chlorides |
| title_sort | enantiomerically enriched tetrahydropyridine allyl chlorides |
| work_keys_str_mv | AT karabiyikoglus enantiomericallyenrichedtetrahydropyridineallylchlorides AT brethomeav enantiomericallyenrichedtetrahydropyridineallylchlorides AT palacint enantiomericallyenrichedtetrahydropyridineallylchlorides AT patonrs enantiomericallyenrichedtetrahydropyridineallylchlorides AT fletchersp enantiomericallyenrichedtetrahydropyridineallylchlorides |