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dc.contributor.authorPalkó, Márta
dc.contributor.authorHänninen, Mikko M.
dc.contributor.authorSillanpää, Reijo
dc.contributor.authorFülöp, Ferenc
dc.date.accessioned2014-09-01T06:57:48Z
dc.date.available2014-09-01T06:57:48Z
dc.date.issued2013
dc.identifier.citationPalkó, M., Hänninen, M. M., Sillanpää, R., & Fülöp, F. (2013). Syntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues. <i>Molecules</i>, <i>18</i>(12), 15080-15093. <a href="https://doi.org/10.3390/molecules181215080" target="_blank">https://doi.org/10.3390/molecules181215080</a>
dc.identifier.otherCONVID_23768509
dc.identifier.otherTUTKAID_62404
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/44140
dc.description.abstractAbstract: Ethyl 2,3- diendo -3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylate ((±)- 1 ) was resolved with O , O '-dibenzoyltartaric acid via diastere omeric salt formation. The efficient synthesis of the enantiomers of 2,3- diendo -3-aminobicyclo[2.2.2]oct- 5-ene-2-carboxylic acid ((+)- 7 and (–)- 7 ), 3- endo -aminobicyclo[2.2.2]oct-5-ene-2- exo -carboxylic acid ((+)- 5 and (–)- 5 ), cis - and trans -3-aminobicyclo[2.2.2]octa ne-2-carboxylic acid ((+)- 6 , (–)- 6 , (+)- 8 and (–)- 8 ) was achieved via isomerization, hydrogenation and hydrolysis of the corresponding esters (–)- 1 and (+)- 1 . The stereochemistry and relative configurations of the synthesized compounds were determined by NMR spectroscopy (based on the 3 J (H,H) coupling constants) and X-ray crystallography.fi
dc.language.isoeng
dc.publisherM D P I AG
dc.relation.ispartofseriesMolecules
dc.relation.urihttp://www.mdpi.com/1420-3049/18/12/15080
dc.subject.otherbicyclic beta-amino acid derivatives
dc.subject.otherconstrained chiral beta-amino acids
dc.subject.otherresolution
dc.subject.othercontinuous flow hydrogenations
dc.titleSyntheses of Four Enantiomers of 2,3-Diendo- and 3-Endo-aminobicyclo[2.2.2]oct-5-ene-2-exo-carboxylic Acid and Their Saturated Analogues
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201408282674
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2014-08-28T03:30:04Z
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange15080-15093
dc.relation.issn1420-3049
dc.relation.numberinseries12
dc.relation.volume18
dc.type.versionpublishedVersion
dc.rights.copyright© 1996-2014 MDPI AG (Basel, Switzerland) unless otherwise stated. This is an article whose final and definitive form has been published by MDPI AG.
dc.rights.accesslevelopenAccessfi
dc.rights.urlhttp://creativecommons.org/licenses/by/3.0/
dc.relation.doi10.3390/molecules181215080
dc.type.okmA1


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© 1996-2014 MDPI AG (Basel, Switzerland) unless otherwise stated. This is an article whose final and definitive form has been published by MDPI AG.
Ellei muuten mainita, aineiston lisenssi on © 1996-2014 MDPI AG (Basel, Switzerland) unless otherwise stated. This is an article whose final and definitive form has been published by MDPI AG.