Iridium-catalyzed reductive nitro-Mannich cyclization.
A new chemoselective reductive nitro-Mannich cyclization reaction sequence of nitroalkyl-tethered lactams has been developed. Relying on the rapid and chemoselective iridium(I)-catalyzed reduction of lactams to the corresponding enamine, subsequent nitro-Mannich cyclization of tethered nitroalkyl fu...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2015
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| _version_ | 1826274051840016384 |
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| author | Gregory, A Chambers, A Hawkins, A Jakubec, P Dixon, D |
| author_facet | Gregory, A Chambers, A Hawkins, A Jakubec, P Dixon, D |
| author_sort | Gregory, A |
| collection | OXFORD |
| description | A new chemoselective reductive nitro-Mannich cyclization reaction sequence of nitroalkyl-tethered lactams has been developed. Relying on the rapid and chemoselective iridium(I)-catalyzed reduction of lactams to the corresponding enamine, subsequent nitro-Mannich cyclization of tethered nitroalkyl functionality provides direct access to important alkaloid natural-product-like structures in yields up to 81 % and in diastereoselectivities that are typically good to excellent. An in-depth understanding of the reaction mechanism has been gained through NMR studies and characterization of reaction intermediates. The new methodology has been applied to the total synthesis of (±)-epi-epiquinamide in four steps. |
| first_indexed | 2024-03-06T22:37:34Z |
| format | Journal article |
| id | oxford-uuid:5a6e77ff-7f54-4c24-a53f-bc57e0f01183 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:37:34Z |
| publishDate | 2015 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:5a6e77ff-7f54-4c24-a53f-bc57e0f011832022-03-26T17:15:44ZIridium-catalyzed reductive nitro-Mannich cyclization.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:5a6e77ff-7f54-4c24-a53f-bc57e0f01183EnglishSymplectic Elements at OxfordWiley2015Gregory, AChambers, AHawkins, AJakubec, PDixon, DA new chemoselective reductive nitro-Mannich cyclization reaction sequence of nitroalkyl-tethered lactams has been developed. Relying on the rapid and chemoselective iridium(I)-catalyzed reduction of lactams to the corresponding enamine, subsequent nitro-Mannich cyclization of tethered nitroalkyl functionality provides direct access to important alkaloid natural-product-like structures in yields up to 81 % and in diastereoselectivities that are typically good to excellent. An in-depth understanding of the reaction mechanism has been gained through NMR studies and characterization of reaction intermediates. The new methodology has been applied to the total synthesis of (±)-epi-epiquinamide in four steps. |
| spellingShingle | Gregory, A Chambers, A Hawkins, A Jakubec, P Dixon, D Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title | Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title_full | Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title_fullStr | Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title_full_unstemmed | Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title_short | Iridium-catalyzed reductive nitro-Mannich cyclization. |
| title_sort | iridium catalyzed reductive nitro mannich cyclization |
| work_keys_str_mv | AT gregorya iridiumcatalyzedreductivenitromannichcyclization AT chambersa iridiumcatalyzedreductivenitromannichcyclization AT hawkinsa iridiumcatalyzedreductivenitromannichcyclization AT jakubecp iridiumcatalyzedreductivenitromannichcyclization AT dixond iridiumcatalyzedreductivenitromannichcyclization |