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Lanthanum-pyBOX complexes as catalysts for the enantioselective conjugate addition of malonate esters to beta-gamma-unsaturated alfa-ketimino esters

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Lanthanum-pyBOX complexes as catalysts for the enantioselective conjugate addition of malonate esters to beta-gamma-unsaturated alfa-ketimino esters

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Espinosa, M.; Blay, G.; Cardona, L.; Fernández, I.; Muñoz Roca, MDC.; Pedro, J. (2018). Lanthanum-pyBOX complexes as catalysts for the enantioselective conjugate addition of malonate esters to beta-gamma-unsaturated alfa-ketimino esters. Journal of Coordination Chemistry. 71(6):864-873. https://doi.org/10.1080/00958972.2018.1437422

Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10251/145998

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Title: Lanthanum-pyBOX complexes as catalysts for the enantioselective conjugate addition of malonate esters to beta-gamma-unsaturated alfa-ketimino esters
Author: Espinosa, M. Blay, G. Cardona, L. Fernández, I. Muñoz Roca, María Del Carmen Pedro, J.R.
UPV Unit: Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada
Issued date:
Abstract:
[EN] In this paper, we report the application of chiral complexes of La(III) with pyBOX ligands as Lewis acid catalysts in the conjugate addition of malonic esters to N-tosyl imines derived from ß,gamma-unsaturated alfa-keto ...[+]
Subjects: Asymmetric catalysis , Lanthanide complexes , Michael addition , Enantioselectivity
Copyrigths: Reserva de todos los derechos
Source:
Journal of Coordination Chemistry. (issn: 0095-8972 )
DOI: 10.1080/00958972.2018.1437422
Publisher:
Taylor & Francis
Publisher version: https://doi.org/10.1080/00958972.2018.1437422
Project ID:
info:eu-repo/grantAgreement/MINECO//CTQ2013-47494-P/ES/NUEVOS RETOS EN EL DESARROLLO DE PROCESOS ENANTIOSELECTIVOS DE FORMACION DE ENLACES C-C MEDIANTE CATALISIS DUAL COOPERATIVA./
Description: "This is an Accepted Manuscript of an article published by Taylor & Francis in Journal of Coordination Chemistry on 2018, available online: https://doi.org/10.1080/00958972.2018.1437422."
Thanks:
This work was supported by the Ministerio de Economia y Competitividad (MINECO-Gobierno de Espana) [grant number CTQ2013-47494-P].
Type: Artículo

References

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De Bettencourt-Dias, A., Barber, P. S., & Bauer, S. (2012). A Water-Soluble Pybox Derivative and Its Highly Luminescent Lanthanide Ion Complexes. Journal of the American Chemical Society, 134(16), 6987-6994. doi:10.1021/ja209572m [+]
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Kodama, H., Ito, J., Hori, K., Ohta, T., & Furukawa, I. (2000). Lanthanide-catalyzed asymmetric 1,3-dipolar cycloaddition of nitrones to alkenes using 3,3′-bis(2-oxazolyl)-1,1′-bi-2-naphthol (BINOL-Box) ligands. Journal of Organometallic Chemistry, 603(1), 6-12. doi:10.1016/s0022-328x(00)00024-3

De Bettencourt-Dias, A., Barber, P. S., & Bauer, S. (2012). A Water-Soluble Pybox Derivative and Its Highly Luminescent Lanthanide Ion Complexes. Journal of the American Chemical Society, 134(16), 6987-6994. doi:10.1021/ja209572m

Comelles, J., Pericas, À., Moreno-Mañas, M., Vallribera, A., Drudis-Solé, G., Lledos, A., … Roces-Fernández, L. (2007). Highly Enantioselective Electrophilic Amination and Michael Addition of Cyclic β-Ketoesters Induced by Lanthanides and (S,S)-ip-pybox:  The Mechanism⊥. The Journal of Organic Chemistry, 72(6), 2077-2087. doi:10.1021/jo0622678

Sanchez-Blanco, A. I., Gothelf, K. V., & Jørgensen, K. A. (1997). Lanthanide-catalyzed endo- and enantioselective 1,3-dipolar cycloaddition reactions of nitrones with alkenes. Tetrahedron Letters, 38(45), 7923-7926. doi:10.1016/s0040-4039(97)10048-x

Desimoni, G., Faita, G., Guala, M., & Pratelli, C. (2003). Different Lanthanide Ions and the Pybox Substituents Induce the Reverse of the Sense of Induction in the Enantioselective Diels−Alder Reaction between Acryloyloxazolidinone and Cyclopentadiene. The Journal of Organic Chemistry, 68(20), 7862-7866. doi:10.1021/jo034215d

Desimoni, G., Faita, G., Filippone, S., Mella, M., Zampori, M. G., & Zema, M. (2001). A new and highly efficient catalyst for the enantioselective Mukaiyama–Michael reaction between ( E )-3-crotonoyl-1,3-oxazolidin-2-one and 2-trimethylsilyloxyfuran. Tetrahedron, 57(51), 10203-10212. doi:10.1016/s0040-4020(01)01055-9

Sammis, G. M., Danjo, H., & Jacobsen, E. N. (2004). Cooperative Dual Catalysis:  Application to the Highly Enantioselective Conjugate Cyanation of Unsaturated Imides. Journal of the American Chemical Society, 126(32), 9928-9929. doi:10.1021/ja046653n

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Espinosa, M., García-Ortiz, A., Blay, G., Cardona, L., Muñoz, M. C., & Pedro, J. R. (2016). E,Z-Stereodivergent synthesis of N-tosyl α,β-dehydroamino esters via a Mukaiyama–Michael addition. RSC Advances, 6(19), 15655-15659. doi:10.1039/c5ra27354d

Espinosa, M., Blay, G., Cardona, L., & Pedro, J. R. (2013). Corrigendum: Asymmetric Conjugate Addition of Malonate Esters to α,β-UnsaturatedN-Sulfonyl Imines: An Expeditious Route to Chiral δ-Aminoesters and Piperidones. Chemistry - A European Journal, 19(52), 17632-17632. doi:10.1002/chem.201304285

X-ray data for compound 3bl: crystallized from hexane-EtOAc; C25H29SN1O8; Mr = 503.55; triclinic; space group = P1; a = 6.2550(2), b = 10.2870(4), c = 11.1380(5) Å; α = 69.333(2), β = 78.688(2), γ = 82.555(2)°; V = 656.11(5) Å3; Z = 1; ρcalcd = 1.274 Mg m−3; μ = 0.170 mm−1; F(0 0 0) = 266. A colorless crystal of 0.04 × 0.08 × 0.08 mm3 was used; 5797 [R(int) = 0.0682] total reflections were collected on a Enraf Nonius Kappa CCD equipped with a graphite monochromator and Mo Kα (λ = 0.71073 Å) radiation. The structures were solved by using direct methods with SHELXS-2014 and refined by using full matrix least squares on F2 with SHELXL-2014 [16]. Non-hydrogen atoms were refined anisotropically and hydrogens were obtained or placed in calculated positions refined by using idealized geometries (riding model) and assigned fixed isotropic displacement parameters. Final values were R = 0.0469 and ωR = 0.1054. CCDC-1581116 contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Parsons, S., Flack, H. D., & Wagner, T. (2013). Use of intensity quotients and differences in absolute structure refinement. Acta Crystallographica Section B Structural Science Crystal Engineering and Materials, 69(3), 249-259. doi:10.1107/s2052519213010014

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