Abstract
We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
Original language | English |
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Pages (from-to) | 8339-8343 |
Number of pages | 5 |
Journal | Organic Letters |
Volume | 21 |
Issue number | 20 |
DOIs | |
Publication status | Published - 2019 Oct 18 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Dive into the research topics of 'Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation'. Together they form a unique fingerprint.Datasets
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CCDC 1561009: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1pdc4l, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pdc4l&sid=DataCite
Dataset
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CCDC 1561010: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1pdc5m, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1pdc5m&sid=DataCite
Dataset
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CCDC 1484673: Experimental Crystal Structure Determination
Liou, Y.-C. (Contributor), Su, Y.-H. (Contributor), Ku, K.-C. (Contributor), Edukondalu, A. (Contributor), Lin, C.-K. (Contributor), Ke, Y.-S. (Contributor), Karanam, P. (Contributor), Lee, C.-J. (Contributor) & Lin, W. (Contributor), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1ltxp0, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1ltxp0&sid=DataCite
Dataset