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http://hdl.handle.net/2445/194109
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DC Field | Value | Language |
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dc.contributor.author | Calbó Zabala, Arnau | - |
dc.contributor.author | Griera Farres, Rosa | - |
dc.contributor.author | Bosch Cartes, Joan | - |
dc.contributor.author | Amat Tusón, Mercedes | - |
dc.date.accessioned | 2023-02-24T10:26:52Z | - |
dc.date.available | 2023-12-14T06:10:25Z | - |
dc.date.issued | 2022-12-14 | - |
dc.identifier.issn | 2052-4129 | - |
dc.identifier.uri | http://hdl.handle.net/2445/194109 | - |
dc.description.abstract | Starting from racemic diastereomeric mixtures of dimethyl-2-oxocyclohexanepropionic acids (4-6) the synthesis of enantiopure 7,8-, 6,8-, and 5,8-dimethyl-substituted cis-decahydroquinolines (11, 13, and 15) and their enantiomers (ent-11, ent-13, and ent-15) is reported. The procedure involves a dynamic kinetic asymmetric transformation in the cyclocondensation of keto-acids 4-6 with (R)-phenylglycinol to give in each case two major oxazoloquinolone lactams (7a/7b, 8a/8b, 9a/9b), which differ in the absolute configuration of all the stereogenic centers except that of the chiral inductor. A subsequent two-step stereoselective removal of the phenylglycinol moiety with simultaneous reduction of the lactam carbonyl affords the enantiopure cis-decahydroquinolines in both enantiomeric series. | - |
dc.format.extent | 6 p. | - |
dc.format.mimetype | application/pdf | - |
dc.language.iso | eng | - |
dc.publisher | Royal Society of Chemistry | - |
dc.relation.isformatof | Versió postprint del document publicat a: https://doi.org/10.1039/D2QO01779B | - |
dc.relation.ispartof | Organic Chemistry Frontiers, 2022, vol. 10, p. 724-729 | - |
dc.relation.uri | https://doi.org/10.1039/D2QO01779B | - |
dc.rights | (c) Calbó Zabala, Arnau et al., 2022 | - |
dc.source | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) | - |
dc.subject.classification | Compostos heterocíclics | - |
dc.subject.classification | Síntesi orgànica | - |
dc.subject.other | Heterocyclic compounds | - |
dc.subject.other | Organic synthesis | - |
dc.title | Cyclocondensation reactions of racemic diastereomers of dimethyl-2-oxocyclohexanepropionic acids with (R)-phenylglycinol: access to both enantiomers of dimethyl cis-decahydroquinolines | - |
dc.type | info:eu-repo/semantics/article | - |
dc.type | info:eu-repo/semantics/acceptedVersion | - |
dc.identifier.idgrec | 730255 | - |
dc.date.updated | 2023-02-24T10:26:52Z | - |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | - |
Appears in Collections: | Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) |
Files in This Item:
File | Description | Size | Format | |
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730255.pdf | 323.65 kB | Adobe PDF | View/Open |
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