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http://hdl.handle.net/10773/18199
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DC Field | Value | Language |
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dc.contributor.author | Sousa, Joana L. C. | pt |
dc.contributor.author | Talhi, Oualid | pt |
dc.contributor.author | Mendes, Ricardo F. | pt |
dc.contributor.author | Almeida Paz, Filipe A. | pt |
dc.contributor.author | Bachari, Khaldoun | pt |
dc.contributor.author | Silva, Artur M. S. | pt |
dc.date.accessioned | 2017-08-01T12:07:35Z | - |
dc.date.issued | 2016-08 | - |
dc.identifier.issn | 1434-193X | pt |
dc.identifier.uri | http://hdl.handle.net/10773/18199 | - |
dc.description.abstract | A one-pot diastereoselective base-catalyzed Michael-initiated ring-closure (MIRC) of activated methyl ketones with 3-bromochromones to give cyclopropa[b]chromanones is described. Three asymmetric centres are generated in the new cyclopropa[b]chromanone skeleton. Stereochemistry studies based on NMR spectroscopy and single-crystal X-ray diffraction analysis revealed the trans configuration of the cyclopropane ring, with the (1R,1aS,7aR)/(1S,1aR,7aS) pair of enantiomers, as was further confirmed by chiral HPLC. The use of acetone in our reaction produced a 1-acetyl-substituted cyclopropa[b]chromanone that can undergo a subsequent MIRC reaction with a second molecule of 3-bromochromone to give the first described 1,1′-carbonylbis(cyclopropa[b]chromanone) dimers as a meso form. | pt |
dc.language.iso | eng | pt |
dc.publisher | Wiley | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/5876/147415/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/5876/147332/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F76407%2F2011/PT | pt |
dc.relation | info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBD%2F84231%2F2012/PT | pt |
dc.rights | restrictedAccess | por |
dc.subject | Oxygen heterocycles | pt |
dc.subject | Cyclopropanes | pt |
dc.subject | Small ring systems | pt |
dc.subject | Fused-ring systems | pt |
dc.subject | Michael addition | pt |
dc.subject | Cyclization | pt |
dc.title | Catalytic one-pot diastereoselective Michael-initiated ring-closure of methyl ketones with 3-bromochromones: synthesis of cyclopropa[b]chromanones | pt |
dc.type | article | - |
dc.peerreviewed | yes | pt |
ua.distribution | international | pt |
degois.publication.firstPage | 3949 | pt |
degois.publication.issue | 23 | pt |
degois.publication.issue | 23 | - |
degois.publication.lastPage | 3958 | pt |
degois.publication.title | European Journal of Organic Chemistry | pt |
degois.publication.volume | 2016 | pt |
dc.date.embargo | 10000-01-01 | - |
dc.identifier.doi | 10.1002/ejoc.201600413 | pt |
Appears in Collections: | CICECO - Artigos |
Files in This Item:
File | Description | Size | Format | |
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Catalytic One-Pot Diastereoselective Michael-Initiated Ring-Closure of Methyl Ketones with 3-Bromochromones Synthesis of Cyclopropa[b]chromanones_10.1002ejoc.201600413.pdf | 755.74 kB | Adobe PDF |
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