Hydrogen borrowing-based methods for the construction of quaternary stereocentres
Compounds containing quaternary stereocentres are a valuable motif in biologically active compounds. Herein we present our strategy to utilise the hydrogen borrowing manifold to access α-quaternary ketones via a tandem acceptorless dehydrogenation-cyclisation cascade. This new application of the met...
| Main Authors: | , , , |
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| Format: | Journal article |
| Language: | English |
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Wiley
2025
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| _version_ | 1824458942811471872 |
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| author | Crompton, J Jenkins, T Rowe, S Donohoe, T |
| author_facet | Crompton, J Jenkins, T Rowe, S Donohoe, T |
| author_sort | Crompton, J |
| collection | OXFORD |
| description | Compounds containing quaternary stereocentres are a valuable motif in biologically active compounds. Herein we present our strategy to utilise the hydrogen borrowing manifold to access α-quaternary ketones via a tandem acceptorless dehydrogenation-cyclisation cascade. This new application of the methodology results in the formation of five- and six-membered carbocycles with a high degree of diastereoselectivity. Interestingly, benzylic alcohol substrates behaved anomalously and eliminated sulfinate in situ to give a set of rearranged α-quaternary ketone products.
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| first_indexed | 2025-02-19T04:33:55Z |
| format | Journal article |
| id | oxford-uuid:e462406b-05ed-4622-a1a9-bc805849e900 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2025-02-19T04:33:55Z |
| publishDate | 2025 |
| publisher | Wiley |
| record_format | dspace |
| spelling | oxford-uuid:e462406b-05ed-4622-a1a9-bc805849e9002025-01-22T13:21:46ZHydrogen borrowing-based methods for the construction of quaternary stereocentresJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:e462406b-05ed-4622-a1a9-bc805849e900EnglishSymplectic ElementsWiley2025Crompton, JJenkins, TRowe, SDonohoe, TCompounds containing quaternary stereocentres are a valuable motif in biologically active compounds. Herein we present our strategy to utilise the hydrogen borrowing manifold to access α-quaternary ketones via a tandem acceptorless dehydrogenation-cyclisation cascade. This new application of the methodology results in the formation of five- and six-membered carbocycles with a high degree of diastereoselectivity. Interestingly, benzylic alcohol substrates behaved anomalously and eliminated sulfinate in situ to give a set of rearranged α-quaternary ketone products. |
| spellingShingle | Crompton, J Jenkins, T Rowe, S Donohoe, T Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title | Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title_full | Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title_fullStr | Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title_full_unstemmed | Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title_short | Hydrogen borrowing-based methods for the construction of quaternary stereocentres |
| title_sort | hydrogen borrowing based methods for the construction of quaternary stereocentres |
| work_keys_str_mv | AT cromptonj hydrogenborrowingbasedmethodsfortheconstructionofquaternarystereocentres AT jenkinst hydrogenborrowingbasedmethodsfortheconstructionofquaternarystereocentres AT rowes hydrogenborrowingbasedmethodsfortheconstructionofquaternarystereocentres AT donohoet hydrogenborrowingbasedmethodsfortheconstructionofquaternarystereocentres |