Oxa-Michael-initiated cascade reactions of levoglucosenone
The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of th...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-10-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.151 |
| _version_ | 1811223270556434432 |
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| author | Julian Klepp Thomas Bousfield Hugh Cummins Sarah V. A.-M. Legendre Jason E. Camp Ben W. Greatrex |
| author_facet | Julian Klepp Thomas Bousfield Hugh Cummins Sarah V. A.-M. Legendre Jason E. Camp Ben W. Greatrex |
| author_sort | Julian Klepp |
| collection | DOAJ |
| description | The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation. |
| first_indexed | 2024-04-12T08:30:02Z |
| format | Article |
| id | doaj.art-dd9308113d4847e585ad245d0b46ed87 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-12T08:30:02Z |
| publishDate | 2022-10-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-dd9308113d4847e585ad245d0b46ed872022-12-22T03:40:14ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-10-011811457146210.3762/bjoc.18.1511860-5397-18-151Oxa-Michael-initiated cascade reactions of levoglucosenoneJulian Klepp0Thomas Bousfield1Hugh Cummins2Sarah V. A.-M. Legendre3Jason E. Camp4Ben W. Greatrex5School of Rural Medicine, University of New England, Armidale, NSW, 2351, Australia Department of Chemical Sciences, School of Applied Sciences, University of Huddersfield, Queensgate, Huddersfield, United Kingdom School of Rural Medicine, University of New England, Armidale, NSW, 2351, Australia School of Rural Medicine, University of New England, Armidale, NSW, 2351, Australia Department of Chemical Sciences, School of Applied Sciences, University of Huddersfield, Queensgate, Huddersfield, United Kingdom School of Rural Medicine, University of New England, Armidale, NSW, 2351, Australia The reactions of aromatic aldehydes and levoglucosenone promoted by methoxide gives bridged α,β-unsaturated ketones, formed by a series of oxa-Michael-initiated cascade reactions in yields of up to 91% (14 examples). A complex series of equilibria operate during the reaction, and the formation of the bridged species is thermodynamically favored, except in the case of 5-methylfurfural and pyrrole-2-carboxaldehyde. This is the first report detailing this type of aldol/Michael cascade involving oxa-Michael initiation.https://doi.org/10.3762/bjoc.18.151cascade reactionsgreen chemistrylevoglucosenoneoxa-michael reaction |
| spellingShingle | Julian Klepp Thomas Bousfield Hugh Cummins Sarah V. A.-M. Legendre Jason E. Camp Ben W. Greatrex Oxa-Michael-initiated cascade reactions of levoglucosenone Beilstein Journal of Organic Chemistry cascade reactions green chemistry levoglucosenone oxa-michael reaction |
| title | Oxa-Michael-initiated cascade reactions of levoglucosenone |
| title_full | Oxa-Michael-initiated cascade reactions of levoglucosenone |
| title_fullStr | Oxa-Michael-initiated cascade reactions of levoglucosenone |
| title_full_unstemmed | Oxa-Michael-initiated cascade reactions of levoglucosenone |
| title_short | Oxa-Michael-initiated cascade reactions of levoglucosenone |
| title_sort | oxa michael initiated cascade reactions of levoglucosenone |
| topic | cascade reactions green chemistry levoglucosenone oxa-michael reaction |
| url | https://doi.org/10.3762/bjoc.18.151 |
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