dc.contributor.author | García Urricelqui, Ane | |
dc.contributor.author | De Cózar Ruano, Abel | |
dc.contributor.author | Mielgo Vicente, María Antonia ![ORCID](/themes/Mirage2//images/orcid_16x16.png) | |
dc.contributor.author | Palomo Nicolau, Claudio | |
dc.date.accessioned | 2024-02-08T10:18:56Z | |
dc.date.available | 2024-02-08T10:18:56Z | |
dc.date.issued | 2020-10-09 | |
dc.identifier.citation | Chemistry - A European Journal 27(7) : 2483-2492 (2021) | |
dc.identifier.issn | 1521-3765 | |
dc.identifier.issn | 0947-6539 | |
dc.identifier.uri | http://hdl.handle.net/10810/65245 | |
dc.description.abstract | The high tendency of α-amino aldehydes to undergo 1,2-additions and their relatively low stability under basic conditions have largely prevented their use as pronucleophiles in the realm of asymmetric catalysis, particularly for the production of quaternary α-amino aldehydes. Herein, it is demonstrated that the chemistry of α-amino aldehydes may be expanded beyond these limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produces densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling leads to the proposal that intramolecular hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde is key for reaction stereocontrol. | |
dc.description.sponsorship | Support has been provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22), Basque Government (GV grant IT1236-19), and Ministerio de Ciencia e Innovación (MINECO, Grant PID2019-109633GB-C21), Spain. | |
dc.language.iso | eng | es_ES |
dc.publisher | Wiley | |
dc.relation | info:eu-repo/grantAgreement/MINECO/PID2019-109633GB-C21 | |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.title | Probing α‐Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α‐Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Brønsted Bases | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.holder | © 2020 Wiley-VCH GmbH | |
dc.relation.publisherversion | https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202004468 | |
dc.identifier.doi | 10.1002/chem.202004468 | |
dc.departamentoes | Química orgánica I | es_ES |
dc.departamentoeu | Kimika organikoa I | es_ES |