dc.contributor.author | Aranzamendi Uruburu, Eider | |
dc.contributor.author | Sotomayor Anduiza, María Nuria | |
dc.contributor.author | Lete Expósito, María Esther | |
dc.date.accessioned | 2024-01-23T07:42:58Z | |
dc.date.available | 2024-01-23T07:42:58Z | |
dc.date.issued | 2017-06-16 | |
dc.identifier.citation | ACS Omega 2(6) : 2706−2718 (2017) | es_ES |
dc.identifier.issn | 2470-1343 | |
dc.identifier.uri | http://hdl.handle.net/10810/64227 | |
dc.description.abstract | An organolithium addition−intramolecular α-
amidoalkylation sequence on N-phenethylimides has been
developed for the synthesis of fused tetrahydroisoquinoline
systems using 1,1′-bi-2-naphthol (binol)-derived Brønsted
acids. This transformation is the first in which activated
benzene derivatives are used as internal nucleophiles, instead
of electron-rich heteroaromatics, generating a quaternary
stereocenter. Phenolic substitution on the aromatic ring of
the phenethylamino moiety and the use of binol-derived N-triflylphosphoramides as catalysts are determinants to achieve
reasonable levels of enantioselection, that is, up to 75% enantiomeric excess, in the α-amidoalkylation step. The procedure is
complementary to the intermolecular α-amidoalkylation process, as opposite enantiomers are formed, and to the Pictet−
Spengler cyclization, which allows the formation of tertiary stereocenters | es_ES |
dc.description.sponsorship | Ministerio de Economíay Competitividad (CTQ2013-41229-P; CTQ2016-74881-P), Gobierno Vasco (IT1045-16) | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | ACS | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/CTQ2013-41229-P | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/CTQ2016-74881-P | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by-nc/3.0/es/ | * |
dc.subject | organocatalysis | es_ES |
dc.subject | Chiral Bronsted acid | es_ES |
dc.subject | asymmetric catalysisi | es_ES |
dc.subject | acyliminium ions | es_ES |
dc.subject | alkaloids | es_ES |
dc.title | Phenolic Activation in Chiral Brønsted Acid-Catalyzed Intramolecular α‑Amidoalkylation Reactions for the Synthesis of Fused Isoquinolines | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2017 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes. | es_ES |
dc.relation.publisherversion | https://doi.org/10.1021/acsomega.7b00170 | es_ES |
dc.identifier.doi | 10.1021/acsomega.7b00170 | |
dc.departamentoes | Química orgánica II | es_ES |
dc.departamentoeu | Kimika organikoa II | es_ES |