Diastereoselective Synthesis of Pyranoquinolines on Zirconium-Containing UiO-66 Metal-Organic Frameworks
[EN] The Zr terephthalate MOFs UiO-66 and UiO-66-NH2 have been found to be highly diastereoselective catalysts for the synthesis of a pyrano[3,2-c]quinoline through an inverse electron -demand aza-Diels-Alder [4+2] cycloaddition of an aryl Qmine (formed in situ from aniline and benzaldehyde) and 3,4-dihydro-2H-pyran in one pot, affording the corresponding trans isomer in diastereomeric excesses of 90-95 %. The solids are stable under the reaction conditions and can be reused at least three times without significant loss of activity or diastereoselectivity. ; Financial support from the Generalitat Valenciana (projects Consolider-Ingenio MULTICAT and AICO/2015/065), the Spanish Ministry of Economy and Competitiveness (MINECO) (program Severn Ochoa SEV20120267), and the Spanish Ministry of Science and Innovation (MICINN) (project MAT2014-52085-C2-1-P) is gratefully acknowledged. V. L. R. thanks the Fundacion "La Caixa" for a "La Caixa-Severo Ochoa" Ph. D. Scholarship. This project received funding from the European Union's Horizon 2020 Tesearch and Innovation Programme under the Marie Skolodowska Curie grant agreement number 641887. ; López-Rechac, V.; García Cirujano, F.; Corma Canós, A.; Llabrés I Xamena, FX. (2016). Diastereoselective Synthesis of Pyranoquinolines on Zirconium-Containing UiO-66 Metal-Organic Frameworks. European Journal of Inorganic Chemistry. 27:4512-4516. https://doi.org/10.1002/ejic.201600372 ; S ; 4512 ; 4516 ; 27 ; Li, B., Wang, H., & Chen, B. (2014). Microporous Metal-Organic Frameworks for Gas Separation. Chemistry - An Asian Journal, 9(6), 1474-1498. doi:10.1002/asia.201400031 ; Li, J.-R., Sculley, J., & Zhou, H.-C. (2011). Metal–Organic Frameworks for Separations. Chemical Reviews, 112(2), 869-932. doi:10.1021/cr200190s ; Rodenas, T., Luz, I., Prieto, G., Seoane, B., Miro, H., Corma, A., … Gascon, J. (2014). Metal–organic framework nanosheets in polymer composite materials for gas separation. Nature Materials, 14(1), 48-55. doi:10.1038/nmat4113 ; Corma, A., García, H., & ...