Intramolecular hydrogen bond activation: Thiourea-organocatalyzed enantioselective 1,3-dipolar cycloaddition of salicylaldehyde-derived azomethine ylides with nitroalkenes
Entity
UAM. Departamento de Química; UAM. Departamento de Química Orgánica; UAM. Instituto de Investigación Avanzada en Ciencias Químicas (IAdChem); UAM. Centro de Investigación en Fisica de la Materia Condensada (IFIMAC)Publisher
American Chemical SocietyDate
2018-01-31Citation
10.1021/acscatal.7b03553
ACS Catalysis 8.3 (2018): 1884-1890
ISSN
2155-5435DOI
10.1021/acscatal.7b03553Funded by
The Spanish Government (CTQ2015-64561-R, CTQ2016- 76061-P) and the European Research Council (ERC-CG, contract number 647550) are acknowledged. We acknowledge the generous allocation of computing time at the CCC (UAM). S.D.-T. gratefully acknowledges the “Ramón y Cajal” program (RYC-2010-07019). Financial support from the Spanish Ministry of Economy and Competitiveness, through the “Maria de Maeztu” Program of Excellence in R&D (MDM- 2014-0377)Project
Gobierno de España. CTQ2015-64561-R; Gobierno de España. CTQ2016- 76061-P; info:eu-repo/grantAgreement/EC/H2020/647550; Gobierno de España. MDM- 2014-0377Editor's Version
http://doi.org/10.1021/acscatal.7b03553Subjects
cycloaddition; hydrogen bond activation; organocatalysis; pyrrolidines; thiourea; QuímicaRights
© 2018 American Chemical Society; This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposeEsta obra está bajo una licencia de Creative Commons Reconocimiento-NoComercial-SinObraDerivada 4.0 Internacional.
Abstract
An organocatalytic strategy for the synthesis of tetrasubstituted pyrrolidines with monoactivated azomethine ylides in high enantiomeric excess and excellent exo/endo selectivity is presented. The key to success is the intramolecular activation via hydrogen bonding through an o-hydroxy group, which allows the dipolar cycloaddition to take place in the presence of azomethine ylides bearing only one activating group. The intramolecular hydrogen bond in the azomethine ylide and the intermolecular hydrogen bond with the catalyst have been demonstrated by DFT calculations and mechanistic proofs to be crucial for the reaction to proceed
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Google Scholar:Esteban, Francisco
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Cieślik, Wioleta
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Arpa González, Enrique Manuel
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Guerrero-Corella, Andrea
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Díaz-Tendero Victoria, Sergio
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Perles, Josefina
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Fernández Salas, José Antonio
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Fraile Carrasco, Alberto
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Alemán Lara, José Julián
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