BODIPY as electron withdrawing group for the activation of double bonds in asymmetric cycloaddition reactions
Entity
UAM. Departamento de Química; UAM. Departamento de Química OrgánicaPublisher
Royal Society of ChemistryDate
2019-03-20Citation
10.1039/c9sc00959k
Chemical Science 10.15 (2019): 4346-4351
ISSN
2041-6520 (print); 2041-6539 (online)DOI
10.1039/c9sc00959kFunded by
Spanish Government (CTQ2015-64561-R, CTQ2016-76061-P), CONACYT (project supported by the Fondo Sectorial de Investigación para la Educación) and PRODEP (Mexico) are acknowledged. We acknowledge allocation of computing time at the CCC-UAM. A. G. C. thanks MINECO (FPI) and T. J. P. CONACYT for PhD fellowships, respectively. A. M. S. thanks CAM for a postdoctoral contract (2016-T2/IND-1660). The authors wish to thank ''Comunidad de Madrid'' for its support to the FotoArt-CM Project (S2018/NMT-4367) through the Program of R&D activities between research groups in Technologies 2013, co-financed by European Structural FundsProject
Gobierno de España. CTQ2015-64561-R; Gobierno de España. CTQ2016-76061-P; Comunidad de Madrid. S2018/NMT-4367/FotoArt-CMEditor's Version
https://doi.org/10.1039/C9SC00959KSubjects
Chemical bonds; Catalysis; Chemical activation; Cycloaddition; Quantum chemistry; QuímicaRights
© The Royal Society of Chemistry 2019Abstract
In this work we have found that a BODIPY can be used as an electron withdrawing group for the activation of double bonds in asymmetric catalysis. The synthesis of cyclohexyl derivatives containing a BODIPY unit can easily be achieved via trienamine catalysis. This allows a new different asymmetric synthesis of BODIPY derivatives and opens the door to future transformation of this useful fluorophore. In addition, the Quantum Chemistry calculations and mechanistic studies provide insights into the role of BODIPY as an EWG
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Google Scholar:Guerrero-Corella, Andrea
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Asenjo-Pascual, Juan
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Pawar, Tushar Janardan
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Díaz-Tendero Victoria, Sergio
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Martín-Somer, Ana
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Gómez, Clarisa Villegas
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Belmonte-Vázquez, José L.
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Ramírez-Ornelas, Diana E.
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Peña-Cabrera, Eduardo
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Fraile Carrasco, Alberto
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Cruz, David Cruz
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Alemán Lara, José Julián
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