Utilize este identificador para referenciar este registo:
https://hdl.handle.net/1822/72937
Registo completo
Campo DC | Valor | Idioma |
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dc.contributor.author | Silva, Natália O. | por |
dc.contributor.author | Abreu, Ana S. | por |
dc.contributor.author | Ferreira, Paula M. T. | por |
dc.contributor.author | Monteiro, Luís S. | por |
dc.contributor.author | Queiroz, Maria João R. P. | por |
dc.date.accessioned | 2021-05-27T15:50:38Z | - |
dc.date.available | 2021-05-27T15:50:38Z | - |
dc.date.issued | 2002-08 | - |
dc.identifier.issn | 1434-193X | por |
dc.identifier.uri | https://hdl.handle.net/1822/72937 | - |
dc.description.abstract | Sulfur analogues of dehydrotryptophan (5-7) were prepared in moderate to good yields (40-80%) by Suzuki cross coupling [Pd(PPh3)(4), Na2CO3 or NaHCO3, DME/H2O, 90 degreesC] of several benzo[b]thiophene boronic acids with the methyl esters of N-tert-butyloxycarbonyl-beta-bromodehydroalanine [Boc-DeltaAla(beta-Br)-OMe] or N-tert-butyloxycarbonyl-beta-bromodehydroaminobutyric acid [Boc-DeltaAbu(beta-Br)-OMe]. The beta-bromodehydroaminoacid precursors 2 were, in turn, synthesized in high yields from the corresponding N,N-diacyldehydroamino acids 1 by treatment with trifluoroacetic acid (TFA) and N-bromosuccinimide (NBS) in two steps or in a one-pot procedure. Both procedures were stereoselective for the E-isomer of Boc-DeltaAla(beta-Br)-OMe. However, for Boc-DeltaAbu(beta-Br)-OMe, different ratios of E/Z isomers were obtained in each procedure. The stereoselectivity for the Z-isomer was increased greatly with the one-pot procedure. Pure isomers were used in the coupling reactions and the stereochemistry of the starting material was generally maintained. | por |
dc.description.sponsorship | The Foundation for Science and Technology (Portugal) is thanked for financial support through IBQF-Univ. Minho, POCTI/99/QUI/32689 project (also financial support of N.O. Silva) and through SFRH/BD/4709/2001 (PhD financial support of A.S. Abreu) | por |
dc.language.iso | eng | por |
dc.publisher | Wiley | por |
dc.relation | POCTI/99/QUI/32689 | por |
dc.rights | openAccess | por |
dc.subject | Amino acids | por |
dc.subject | Sulfur heterocycles | por |
dc.subject | Suzuki coupling | por |
dc.subject | Stereoisomerism | por |
dc.title | Synthesis using Suzuki cross couplings of sulfur analogues of dehydrotryptophan with a definite stereochemistry | por |
dc.type | article | - |
dc.peerreviewed | yes | por |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/journal/10990690 | por |
oaire.citationStartPage | 2524 | por |
oaire.citationEndPage | 2528 | por |
oaire.citationIssue | 15 | por |
dc.date.updated | 2021-05-24T15:29:41Z | - |
dc.identifier.eissn | 1099-0690 | por |
dc.identifier.doi | 10.1002/1099-0690(200208)2002:15<2524::AID-EJOC2524>3.0.CO;2-W | por |
dc.subject.wos | Science & Technology | - |
sdum.export.identifier | 10843 | - |
sdum.journal | European Journal of Organic Chemistry | por |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2002-Eur. J. Org. Chem. 2524.pdf | 118,06 kB | Adobe PDF | Ver/Abrir |