Carceller-Ferrer, L.; González Del Campo, A.; Vila, C.; Blay, G.; Muñoz Roca, MDC.; Pedro, JR. (2022). Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones. Journal of Organic Chemistry. 87(7):4538-4549. https://doi.org/10.1021/acs.joc.1c02817
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/194771
Title:
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Catalytic Diastereo- and Enantioselective Synthesis of Tertiary Trifluoromethyl Carbinols through a Vinylogous Aldol Reaction of Alkylidenepyrazolones with Trifluoromethyl Ketones
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Author:
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Carceller-Ferrer, Laura
González del Campo, Aleix
Vila, Carlos
Blay, Gonzalo
Muñoz Roca, María Del Carmen
Pedro, José R.
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UPV Unit:
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Universitat Politècnica de València. Escuela Técnica Superior de Ingeniería del Diseño - Escola Tècnica Superior d'Enginyeria del Disseny
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Issued date:
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Abstract:
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[EN] A diastereo- and enantioselective organocatalyticaldol reaction between alkylidenepyrazolones and trifluoromethylketones leading to chiral tertiary alcohols bearing a trifluoromethylgroup is presented. The methodology ...[+]
[EN] A diastereo- and enantioselective organocatalyticaldol reaction between alkylidenepyrazolones and trifluoromethylketones leading to chiral tertiary alcohols bearing a trifluoromethylgroup is presented. The methodology is based on the use of abifunctional organocatalyst in order to activate the gamma-hydrogenatoms of the alkylidenepyrazolone nucleophile and the carbonylgroup of the trifluoromethylarylketone providing highly functionalized trifluoromethyl alcohols with moderate yields, excellentdiastereoselectivity, and moderate to good enantioselectivity. Experiments monitoring the conversion by1H NMR and theenantiomeric excess by HPLC with the reaction time showed that full conversion of the starting materials is not achieved and thatthe enantiomeric excess decreases upon extended times, probably due to the reversibility of the reaction.
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Copyrigths:
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Reconocimiento (by)
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Source:
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Journal of Organic Chemistry. (issn:
0022-3263
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DOI:
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10.1021/acs.joc.1c02817
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Publisher:
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American Chemical Society
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Publisher version:
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https://doi.org/10.1021/acs.joc.1c02817
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Project ID:
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info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-116944GB-I00/ES/ESTRATEGIAS CATALITICAS ASIMETRICAS PARA LA SINTESIS DE NUEVAS ENTIDADES QUIMICAS QUIRALES CON POTENCIAL INTERES FARMACOLOGICO/
info:eu-repo/grantAgreement/MCIU//RYC-2016-20187//Ayudas para contratos Ramón y Cajal/
info:eu-repo/grantAgreement/CIUCSD//AICO%2F2020%2F68/
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Thanks:
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Financial support from Grant PID2020-116944GB funded by MCIN/AEI/10.13039/501100011033 and by "ERDF A way of making Europe" and AICO/2020/68 funded by Conselleria d'Innovacio, Universitat, Ciencia i Societat Digital ...[+]
Financial support from Grant PID2020-116944GB funded by MCIN/AEI/10.13039/501100011033 and by "ERDF A way of making Europe" and AICO/2020/68 funded by Conselleria d'Innovacio, Universitat, Ciencia i Societat Digital (AICO/2020/68) are acknowledged. L.C.-F. thanks the Universitat de Valencia for a predoctoral grant. C.V. thanks the RyC contract (Grant RYC-2016-20187) funded by MCIN/AEI/10.13039/501100011033 and by "European Union Next GenerationEU/PRTR". Access to NMR, MS, and X-ray facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged.
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Type:
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Artículo
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