Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes
dc.contributor.author | Vera Salas, Silvia | |
dc.contributor.author | Landa Álvarez, Aitor | |
dc.contributor.author | Mielgo Vicente, María Antonia | |
dc.contributor.author | Gamboa Landa, José Ignacio | |
dc.contributor.author | Oyarbide Garmendia, Juan Miguel | |
dc.contributor.author | Soloshonok, Vadym Anatolievch | |
dc.date.accessioned | 2023-03-29T13:47:53Z | |
dc.date.available | 2023-03-29T13:47:53Z | |
dc.date.issued | 2023-03-16 | |
dc.identifier.citation | Molecules 28(6) : (2023) // Article ID 2694 | es_ES |
dc.identifier.issn | 1420-3049 | |
dc.identifier.uri | http://hdl.handle.net/10810/60550 | |
dc.description.abstract | Aldehydes constitute a main class of organic compounds widely applied in synthesis. As such, catalyst-controlled enantioselective α-functionalization of aldehydes has attracted great interest over the years. In this context, α-branched aldehydes are especially challenging substrates because of reactivity and selectivity issues. Firstly, the transient trisubstituted enamines and enolates resulting upon treatment with an aminocatalyst or a base, respectively, would exhibit attenuated reactivity; secondly, mixtures of E- and Z-configured enamines/enolates may be formed; and third, effective face-discrimination on such trisubstituted sp2 carbon intermediates by the incoming electrophilic reagent is not trivial. Despite these issues, in the last 15 years, several catalytic approaches for the α-functionalization of prostereogenic α-branched aldehydes that proceed in useful yields and diastereo- and enantioselectivity have been uncovered. Developments include both organocatalytic and metal-catalyzed approaches as well as dual catalysis strategies for forging new carbon–carbon and carbon–heteroatom (C-O, N, S, F, Cl, Br, …) bond formation at Cα of the starting aldehyde. In this review, some key early contributions to the field are presented, but focus is on the most recent methods, mainly covering the literature from year 2014 onward. | es_ES |
dc.description.sponsorship | This research was funded by Basque Government (grant IT-1583-22) and by MCIN/AEI/10.13039/501100011033 (grant PID2019-109633GB-C21). | es_ES |
dc.language.iso | eng | es_ES |
dc.publisher | MDPI | es_ES |
dc.relation | info:eu-repo/grantAgreement/MICINN/PID2019-109633GB-C21 | es_ES |
dc.rights | info:eu-repo/semantics/openAccess | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | |
dc.subject | aldehydes | es_ES |
dc.subject | asymmetric catalysis | es_ES |
dc.subject | quaternary carbon | es_ES |
dc.subject | organocatalysis | es_ES |
dc.subject | dual catalysis | es_ES |
dc.subject | reaction umpolung | es_ES |
dc.title | Catalytic Asymmetric α-Functionalization of α-Branched Aldehydes | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.date.updated | 2023-03-28T12:56:43Z | |
dc.rights.holder | © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/). | es_ES |
dc.relation.publisherversion | https://www.mdpi.com/1420-3049/28/6/2694 | es_ES |
dc.identifier.doi | 10.3390/molecules28062694 | |
dc.departamentoes | Química orgánica I | |
dc.departamentoeu | Kimika organikoa I |
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Except where otherwise noted, this item's license is described as © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/ 4.0/).