dc.contributor.author | Izquierdo, June | |
dc.contributor.author | Demurget, Noémie | |
dc.contributor.author | Landa Alvarez, Aitor | |
dc.contributor.author | Brinck, Tore | |
dc.contributor.author | Mercero Larraza, José María | |
dc.contributor.author | Dinér, Peter | |
dc.contributor.author | Oyarbide Garmendia, Juan Miguel | |
dc.contributor.author | Palomo Nicolau, Claudio | |
dc.date.accessioned | 2024-06-10T18:00:52Z | |
dc.date.available | 2024-06-10T18:00:52Z | |
dc.date.issued | 2019-07-18 | |
dc.identifier.citation | Chemistry – A European Journal 25(53) : 12431-12438 (2019) | es_ES |
dc.identifier.issn | 0947-6539 | |
dc.identifier.uri | http://hdl.handle.net/10810/68398 | |
dc.description.abstract | A bifunctional amine/squaramide catalyst promoted direct aldol addition of an hydantoin surrogate to pyridine 2-carbaldehyde N-oxides to afford adducts bearing two vicinal tertiary/quaternary carbons in high diastereo- and enantioselectivity (d.r. up to >20:1; ee up to 98%) is reported. Acid hydrolysis of adducts followed by reduction of the N-oxide group yields enantiopure carbinol-tethered quaternary hydantoin-azaarene conjugates with densely functionalized skeletons. DFT studies of the potential energy surface
(B3LYP/6–31+G(d)+CPCM (dichloromethane)) of the reaction correlate the activity of different catalysts and support an intramolecular hydrogen-bond-assisted activation of the squaramide moiety in the transition state of the catalytic reaction. | es_ES |
dc.description.sponsorship | Financial support was provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22), Basque Government (Grant No IT-1236-19), and Ministerio de Economía y Competitividad (MEC, Grant CTQ2016-78487-C2), Spain. We thank SGiker (UPV/EHU) for providing NMR, HRMS, X-ray, and Computational resources. T.B. and P.D. thank KTH-Royal Institute of Technology for financial support and the National Supercomputer Center (NSC) in Linköping for computational resources. | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley-VCH | es_ES |
dc.relation | info:eu-repo/grantAgreement/MINECO/CTQ2016-78487-C2 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.subject | asymmetric synthesis | es_ES |
dc.subject | organocatalysis | es_ES |
dc.subject | aldol reaction | es_ES |
dc.subject | Brønsted base | es_ES |
dc.title | Asymmetric Synthesis of Adjacent Tri- and Tetrasubstituted Carbon Stereocenters: Organocatalytic Aldol Reaction of an Hydantoin Surrogate with Azaarene 2-Carbaldehydes | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim | es_ES |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.201902817 | es_ES |
dc.identifier.doi | 10.1002/chem.201902817 | |
dc.departamentoes | Química Orgánica e Inorgánica | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |