Intramolecular hydrogen bond activation for kinetic resolution of furanone derivatives by an organocatalyzed [3+2] asymmetric cycloaddition
Entity
UAM. Departamento de Física de la Materia Condensada; UAM. Departamento de Química; UAM. Departamento de Química Física Aplicada; UAM. Departamento de Química OrgánicaPublisher
Royal Society of ChemistryDate
2023-10-11Citation
10.1039/D3QO01471A
Organic Chemistry Frontiers (2023): 11st October
ISSN
2052-4129 (online)DOI
10.1039/D3QO01471AFunded by
PID2019-110091GB-I00, PID2021-122299NB-I00, TED2021-130470B-I00, TED2021-129999B-C32, “Comunidad de Madrid” for European Structural Funds (S2018/NMT-4367) and (Y2020/NMT6469), CEX2018-000805-MProject
Gobierno de España. PID2019-110091GB-I00; Gobierno de España. PID2021-122299NB-I00; Gobierno de España. TED2021-130470B-I00; Gobierno de España. TED2021-129999B-C32; Comunidad de Madrid. S2018/NMT-4367/FotoArt-CM; Comunidad de Madrid. Y2020/NMT-6469/FOTOSURF-CM; Gobierno de España. CEX2018-000805-MEditor's Version
https://doi.org/10.1039/D3QO01471ASubjects
Intramolecular Hydrogen; Furanone; Cycloaddition; Física; QuímicaRights
© 2023 M. A. Valle-Amores et al.Abstract
Herein, a formal highly enantioselective organocatalyzed [3+2] cycloaddition of furanone derivatives and azomethine ylides is presented. The success of this reaction resides in an intramolecular hydrogen bond activation through an o-hydroxy group at aromatic ring of the imine, allowing the formation of highly multifunctional bicyclic adducts with five stereogenic centers in a stereocontrolled manner. Furthermore, the reaction is paired to a highly efficient kinetic resolution of butenolides, achieving selectivity factors above 200. Using this methodology, furan-2(5H)-ones as well as furo[3,4-c]pyrrolidinones were obtained with high enantioselectivities. Quantum chemistry calculations reveal the crucial role of hydrogen bond formed between the catalyst donor-units and the two reagents, which modify their arrangement and promote effective facial discrimination resulting in a highly selective kinetic resolution. In addition, further applicability of the kinetic resolution process is shown
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Google Scholar:Valle-Amores, Miguel A.
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Feberero, Claudia
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Martín Somer, Ana
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Díaz-Tendero Victoria, Sergio
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Smith, Andrew D.
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Fraile Carrasco, Alberto
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Alemán Lara, José Julián
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