Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones
The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a c...
| Main Authors: | , , , , , , |
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| Formato: | Journal article |
| Idioma: | English |
| Publicado: |
Royal Society of Chemistry
2020
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| _version_ | 1826312059057340416 |
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| author | Zhang, L Yamazaki, K Leitch, JA Manzano, R Atkinson, AM Hamlin, TA Dixon, DJ |
| author_facet | Zhang, L Yamazaki, K Leitch, JA Manzano, R Atkinson, AM Hamlin, TA Dixon, DJ |
| author_sort | Zhang, L |
| collection | OXFORD |
| description | The construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(I) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations. |
| first_indexed | 2024-03-07T08:20:30Z |
| format | Journal article |
| id | oxford-uuid:a1ccded9-f45f-453e-b127-fa2bfcbb1e2e |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T08:20:30Z |
| publishDate | 2020 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:a1ccded9-f45f-453e-b127-fa2bfcbb1e2e2024-01-29T12:33:52ZDual catalytic enantioselective desymmetrization of allene-tethered cyclohexanonesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:a1ccded9-f45f-453e-b127-fa2bfcbb1e2eEnglishExternalRoyal Society of Chemistry2020Zhang, LYamazaki, KLeitch, JAManzano, RAtkinson, AMHamlin, TADixon, DJThe construction of enantioenriched azabicyclo[3.3.1]nonan-6-one heterocycles via an enantioselective desymmetrization of allene-linked cyclohexanones, enabled through a dual catalytic system, that provides synchronous activation of the cyclohexanone with a chiral prolinamide and the allene with a copper(I) co-catalyst to deliver the stereodefined bicyclic core, is described. Successful application to oxygen analogues was also achieved, thereby providing a new enantioselective synthetic entry to architecturally complex bicyclic ethereal frameworks. The mechanistic pathway and the origin of enantio- and diastereoselectivities has been uncovered using density functional theory (DFT) calculations. |
| spellingShingle | Zhang, L Yamazaki, K Leitch, JA Manzano, R Atkinson, AM Hamlin, TA Dixon, DJ Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title | Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title_full | Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title_fullStr | Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title_full_unstemmed | Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title_short | Dual catalytic enantioselective desymmetrization of allene-tethered cyclohexanones |
| title_sort | dual catalytic enantioselective desymmetrization of allene tethered cyclohexanones |
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