Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis
The first examples of ynamide hydroacylation are described. Using rhodium catalysis, linear β-enaminone products are generated in high yield and excellent regioselectivity from the combination of aldehydes and ynamides. The enaminone products are subsequently used as a platform to construct a divers...
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| Format: | Journal article |
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Royal Society of Chemistry
2017
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| _version_ | 1826292324139794432 |
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| author | Straker, R Majhail, M Willis, M |
| author_facet | Straker, R Majhail, M Willis, M |
| author_sort | Straker, R |
| collection | OXFORD |
| description | The first examples of ynamide hydroacylation are described. Using rhodium catalysis, linear β-enaminone products are generated in high yield and excellent regioselectivity from the combination of aldehydes and ynamides. The enaminone products are subsequently used as a platform to construct a diverse array of substituted pyrazoles, pyrimidines, and isoxazoles in a two-step, one-pot sequence. It was found that with judicious choice of catalyst system it was possible to overturn the regioselectivity of the hydroacylation reaction to generate α-enaminone products. |
| first_indexed | 2024-03-07T03:12:55Z |
| format | Journal article |
| id | oxford-uuid:b4d0496e-1a4c-411e-8b8a-444f0887d011 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T03:12:55Z |
| publishDate | 2017 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | oxford-uuid:b4d0496e-1a4c-411e-8b8a-444f0887d0112022-03-27T04:28:51ZExploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesisJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:b4d0496e-1a4c-411e-8b8a-444f0887d011Symplectic Elements at OxfordRoyal Society of Chemistry2017Straker, RMajhail, MWillis, MThe first examples of ynamide hydroacylation are described. Using rhodium catalysis, linear β-enaminone products are generated in high yield and excellent regioselectivity from the combination of aldehydes and ynamides. The enaminone products are subsequently used as a platform to construct a diverse array of substituted pyrazoles, pyrimidines, and isoxazoles in a two-step, one-pot sequence. It was found that with judicious choice of catalyst system it was possible to overturn the regioselectivity of the hydroacylation reaction to generate α-enaminone products. |
| spellingShingle | Straker, R Majhail, M Willis, M Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title | Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title_full | Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title_fullStr | Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title_full_unstemmed | Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title_short | Exploiting rhodium-catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| title_sort | exploiting rhodium catalysed ynamide hydroacylation as a platform for divergent heterocycle synthesis |
| work_keys_str_mv | AT strakerr exploitingrhodiumcatalysedynamidehydroacylationasaplatformfordivergentheterocyclesynthesis AT majhailm exploitingrhodiumcatalysedynamidehydroacylationasaplatformfordivergentheterocyclesynthesis AT willism exploitingrhodiumcatalysedynamidehydroacylationasaplatformfordivergentheterocyclesynthesis |