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
| dc.contributor.author | Palkó, Márta | |
| dc.contributor.author | Hänninen, Mikko M. | |
| dc.contributor.author | Sillanpää, Reijo | |
| dc.contributor.author | Fülöp, Ferenc | |
| dc.date.accessioned | 2014-09-01T06:57:48Z | |
| dc.date.available | 2014-09-01T06:57:48Z | |
| dc.date.issued | 2013 | |
| dc.identifier.citation | Palkó, 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.other | CONVID_23768509 | |
| dc.identifier.other | TUTKAID_62404 | |
| dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/44140 | |
| dc.description.abstract | Abstract: 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.iso | eng | |
| dc.publisher | M D P I AG | |
| dc.relation.ispartofseries | Molecules | |
| dc.relation.uri | http://www.mdpi.com/1420-3049/18/12/15080 | |
| dc.subject.other | bicyclic beta-amino acid derivatives | |
| dc.subject.other | constrained chiral beta-amino acids | |
| dc.subject.other | resolution | |
| dc.subject.other | continuous flow hydrogenations | |
| dc.title | 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 | |
| dc.type | article | |
| dc.identifier.urn | URN:NBN:fi:jyu-201408282674 | |
| dc.contributor.laitos | Kemian laitos | fi |
| dc.contributor.laitos | Department of Chemistry | en |
| dc.contributor.oppiaine | Epäorgaaninen ja analyyttinen kemia | fi |
| dc.contributor.oppiaine | Inorganic and Analytical Chemistry | en |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
| dc.date.updated | 2014-08-28T03:30:04Z | |
| dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
| dc.description.reviewstatus | peerReviewed | |
| dc.format.pagerange | 15080-15093 | |
| dc.relation.issn | 1420-3049 | |
| dc.relation.numberinseries | 12 | |
| dc.relation.volume | 18 | |
| dc.type.version | publishedVersion | |
| 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.accesslevel | openAccess | fi |
| dc.rights.url | http://creativecommons.org/licenses/by/3.0/ | |
| dc.relation.doi | 10.3390/molecules181215080 | |
| dc.type.okm | A1 |
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