Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach
A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane produc...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
| Published: |
Elsevier
2019
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| _version_ | 1797068837366005760 |
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| author | Armstrong, RJ Akhtar, WM Frost, JR Christensen, KE Stevenson, NG Donohoe, TJ |
| author_facet | Armstrong, RJ Akhtar, WM Frost, JR Christensen, KE Stevenson, NG Donohoe, TJ |
| author_sort | Armstrong, RJ |
| collection | OXFORD |
| description | A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled. |
| first_indexed | 2024-03-06T22:15:48Z |
| format | Journal article |
| id | oxford-uuid:53584a2c-c316-4b99-81a1-f45cbe990b86 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T22:15:48Z |
| publishDate | 2019 |
| publisher | Elsevier |
| record_format | dspace |
| spelling | oxford-uuid:53584a2c-c316-4b99-81a1-f45cbe990b862022-03-26T16:31:05ZStereoselective synthesis of alicyclic ketones: a hydrogen borrowing approachJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:53584a2c-c316-4b99-81a1-f45cbe990b86EnglishSymplectic Elements at OxfordElsevier2019Armstrong, RJAkhtar, WMFrost, JRChristensen, KEStevenson, NGDonohoe, TJA highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled. |
| spellingShingle | Armstrong, RJ Akhtar, WM Frost, JR Christensen, KE Stevenson, NG Donohoe, TJ Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title | Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title_full | Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title_fullStr | Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title_full_unstemmed | Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title_short | Stereoselective synthesis of alicyclic ketones: a hydrogen borrowing approach |
| title_sort | stereoselective synthesis of alicyclic ketones a hydrogen borrowing approach |
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