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. 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