Fluorination Homologation of Biorenewable Synthon Cyrene
A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reacting it with an in situ-generated difluorocarbene, an...
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MDPI AG
2024-12-01
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| Online Access: | https://www.mdpi.com/1422-8599/2024/4/M1929 |
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| author | Johannes Puschnig Ben W. Greatrex |
| author_facet | Johannes Puschnig Ben W. Greatrex |
| author_sort | Johannes Puschnig |
| collection | DOAJ |
| description | A one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reacting it with an in situ-generated difluorocarbene, and then heating it to ring-open the cyclopropane. Access to the product provides access to fluorinated analogues of this valuable chiral biomass derivative. |
| format | Article |
| id | doaj-art-ec01a57b6ad447f29d309fdcbbc58c9c |
| institution | DOAJ |
| issn | 1422-8599 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
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| series | Molbank |
| spelling | doaj-art-ec01a57b6ad447f29d309fdcbbc58c9c2025-08-20T02:43:20ZengMDPI AGMolbank1422-85992024-12-0120244M192910.3390/M1929Fluorination Homologation of Biorenewable Synthon CyreneJohannes Puschnig0Ben W. Greatrex1Faculty of Medicine and Health, University of New England, Armidale, NSW 2351, AustraliaFaculty of Medicine and Health, University of New England, Armidale, NSW 2351, AustraliaA one-carbon difluorocyclopropanation/ring-expansion has been developed for the chiral synthon Cyrene, which is obtained via cellulose pyrolysis. The ring-enlargement was achieved by converting Cyrene (dihydrolevoglucosenone) into an enamine, reacting it with an in situ-generated difluorocarbene, and then heating it to ring-open the cyclopropane. Access to the product provides access to fluorinated analogues of this valuable chiral biomass derivative.https://www.mdpi.com/1422-8599/2024/4/M1929ring expansiondifluorocyclopropanegreen chemistrylevoglucosenonecyrene |
| spellingShingle | Johannes Puschnig Ben W. Greatrex Fluorination Homologation of Biorenewable Synthon Cyrene Molbank ring expansion difluorocyclopropane green chemistry levoglucosenone cyrene |
| title | Fluorination Homologation of Biorenewable Synthon Cyrene |
| title_full | Fluorination Homologation of Biorenewable Synthon Cyrene |
| title_fullStr | Fluorination Homologation of Biorenewable Synthon Cyrene |
| title_full_unstemmed | Fluorination Homologation of Biorenewable Synthon Cyrene |
| title_short | Fluorination Homologation of Biorenewable Synthon Cyrene |
| title_sort | fluorination homologation of biorenewable synthon cyrene |
| topic | ring expansion difluorocyclopropane green chemistry levoglucosenone cyrene |
| url | https://www.mdpi.com/1422-8599/2024/4/M1929 |
| work_keys_str_mv | AT johannespuschnig fluorinationhomologationofbiorenewablesynthoncyrene AT benwgreatrex fluorinationhomologationofbiorenewablesynthoncyrene |