Martinez-Pardo, P.; Blay, G.; Vila, C.; Sanz-Marco, A.; Muñoz Roca, MDC.; Pedro, JR. (2019). Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis. The Journal of Organic Chemistry. 84(1):314-325. https://doi.org/10.1021/acs.joc.8b02808
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/147736
Title:
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Enantioselective Synthesis of 5-Trifluoromethyl-2-oxazolines under Dual Silver/Organocatalysis
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Author:
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Martinez-Pardo, Pablo
Blay, Gonzalo
Vila, Carlos
Sanz-Marco, Amparo
Muñoz Roca, María Del Carmen
Pedro, Jose R.
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UPV Unit:
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Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
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Issued date:
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Abstract:
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[EN] The first enantioselective formal [3 + 2] cycloaddition between ¿-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a ...[+]
[EN] The first enantioselective formal [3 + 2] cycloaddition between ¿-isocyanoesters and trifluoromethylketones to give 5-trifluoromethyl-2-oxazolines bearing two contiguous stereogenic centers, one of them being a quaternary stereocenter substituted with a CF3 group, has been developed. The reaction is based upon a multicatalytic approach that combines a bifunctional Brønsted base-squaramide organocatalyst and Ag+ as Lewis acid. The reaction could be achieved with a range of aryl and heteroaryl trifluoromethyl ketones, and the resulting oxazolines were obtained with good to excellent diastereo- and enantioselectivity.
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Copyrigths:
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Reserva de todos los derechos
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Source:
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The Journal of Organic Chemistry. (issn:
0022-3263
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DOI:
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10.1021/acs.joc.8b02808
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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.8b02808
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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 2013-2016/CTQ2017-84900-P/ES/REACCIONES DE ADICION ENANTIOSELECTIVAS MEDIANTE SISTEMAS MULTICATALITICOS. HERRAMIENTAS PARA LA SINTESIS EFICIENTE DE MOLECULAS CON ACTIVIDAD FARMACOLOGICA/
info:eu-repo/grantAgreement/MINECO//RYC-2016-20187/
info:eu-repo/grantAgreement/GVA//APOSTD%2F2016%2F139/
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Thanks:
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Financial support from the MINECO and FEDER (CTQ2017-84900-P). Access to NMR and MS facilities from SCSIE-UV. C.V. thanks the Spanish Government for a Ramon y Cajal contract (RyC-2016-20187). A.S.-M. thanks the Generalitat ...[+]
Financial support from the MINECO and FEDER (CTQ2017-84900-P). Access to NMR and MS facilities from SCSIE-UV. C.V. thanks the Spanish Government for a Ramon y Cajal contract (RyC-2016-20187). A.S.-M. thanks the Generalitat Valenciana and Fondo Social Europeo for a postdoctoral grant (APOST/2016/139).
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Type:
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Artículo
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