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α-Hydroxy ketones as masked ester donors in Brønsted base catalyzed conjugate additions to nitroalkenes

Identificadores del recurso

Olaizola, I., Campano, T. E., Iriarte, I., Vera, S., Mielgo, A., García, J. M., Odriozola, J. M., Oiarbide, M., & Palomo, C. (2018). Α‐hydroxy ketones as masked ester donors in brønsted base catalyzed conjugate additions to nitroalkenes. Chemistry – A European Journal, 24(15), 3893-3901. https://doi.org/10.1002/chem.201705968

0947-6539

10.1002/chem.201705968

https://academica-e.unavarra.es/handle/2454/47253

Procedència

(Academica-e: repositorio digital de la Universidad Pública de Navarra)

Fitxa

Títol:: α-Hydroxy ketones as masked ester donors in Brønsted base catalyzed conjugate additions to nitroalkenes
Tema:: Addition; Asymmetric catalysis; Esters; Organocatalysis; Synthesis design
Descripció:: The catalyst-controlled enantioselective direct addition reaction of enolizable esters and related carboxylic acid derivatives to p electrophiles remains a difficult synthetic transformation. In this study, the suitability of a-hydroxy ketones as ester equivalents capable of being activated by bifunctional Brønsted base catalysts in the context of conjugate addition reactions to nitroolefins is demonstrated. The scope of the reaction, which affords the corresponding Michael adducts with very high stereoselectivity (diastereomeric ratio (d.r.) +95:5, up to 99% enantiomeric excess (ee)), and its limitations are explored, as is the aftermath elaboration of adducts into densely functionalized enantioenriched products.; There is now growing evidence that parkinsonism and other extrapyramidal signs are highly prevalent in patients with first-episode psychosis who have never been exposed to antipsychotic drugs. However, the neurocognitive correlates of parkinsonism in this population remained to be clarified. A sample comprising 100 consecutive drug-naive patients with first-episode psychosis were enrolled on the study and followed up for 6 months. Seventy-seven completed assessments at 3 time points (baseline, 1 mo, and 6 mo), involving clinical and cognitive examinations and a specific assessment of motor abnormalities. The Simpson-Angus Scale (SAS) was used for the assessment of extrapyramidal signs, and each motor domain was evaluated with a standard assessment scale. Linear mixed models were built to explore the longitudinal relationships between parkinsonism scores and cognitive impairment. Parkinsonism scores showed significant strong longitudinal associations with deficits in memory, executive functioning, and attention. Spontaneous parkinsonism (total SAS score and hypokinesia and rigidity subscores at baseline) showed high 6-month predictive values for cognitive impairment. In addition, they also had high predictive values for neurologic soft-sign abnormalities but not for dyskinesia, akathisia, and pure catatonic abnormalities. No predictive value was found for glabella-salivation or tremor subscores on the SAS scale. These results emphasize the relevance of the assessment of parkinsonism signs prior to starting to administer antipsychotic drugs, as core manifestations of psychotic illness with a high predictive value for cognitive impairment.; Support has been provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22); the Basque Government (GV grant No IT-628-13); and the Ministerio de Economía y Competitividad (MEC Grant CTQ2016-78487-C2), Spain. I.O. thanks UPV/EHU for a fellowship, and T.C. thanks MEC for a FPI Grant.
Idioma:: English
Relació:: Chemistry - A European Journal 2018, 24, 3893 – 3901; info:eu-repo/grantAgreement/MINECO//CTQ2016-78487-C2; https://doi.org/10.1002/chem.201705968
Autor/Productor:: Olaizola, Iurre; Campano, Teresa E.; Iriarte, Igor; Vera, Silvia; Mielgo, Antonia; García Castillo, Jesús María; Odriozola Ibarguren, José Manuel; Oiarbide, Mikel; Palomo, Claudio
Editor:: Wiley
Otros colaboradores/productores:: Institute for Advanced Materials and Mathematics - INAMAT2; Química Aplicada; Kimika Aplikatua
Drets:: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim; info:eu-repo/semantics/openAccess
Data:: 2018
Tipo de recurso:: info:eu-repo/semantics/article; Versión aceptada / Onetsi den bertsioa; info:eu-repo/semantics/acceptedVersion
Format:: application/pdf

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2. <dc:creator>Olaizola, Iurre</dc:creator>
3. <dc:creator>Campano, Teresa E.</dc:creator>
4. <dc:creator>Iriarte, Igor</dc:creator>
5. <dc:creator>Vera, Silvia</dc:creator>
6. <dc:creator>Mielgo, Antonia</dc:creator>
7. <dc:creator>García Castillo, Jesús María</dc:creator>
8. <dc:creator>Odriozola Ibarguren, José Manuel</dc:creator>
9. <dc:creator>Oiarbide, Mikel</dc:creator>
10. <dc:creator>Palomo, Claudio</dc:creator>
11. <dc:contributor>Institute for Advanced Materials and Mathematics - INAMAT2</dc:contributor>
12. <dc:contributor>Química Aplicada</dc:contributor>
13. <dc:contributor>Kimika Aplikatua</dc:contributor>
14. <dc:subject>Addition</dc:subject>
15. <dc:subject>Asymmetric catalysis</dc:subject>
16. <dc:subject>Esters</dc:subject>
17. <dc:subject>Organocatalysis</dc:subject>
18. <dc:subject>Synthesis design</dc:subject>
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13. <dc:contributor>Kimika Aplikatua</dc:contributor>
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