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Esteban F, Cieślik W, Arpa EM, et al. Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes. ACS Catal. 2018;8(3):1884-1890doi: 10.1021/acscatal.7b03553.
Esteban, F., Cieślik, W., Arpa, E. M., Guerrero-Corella, A., Díaz-Tendero, S., Perles, J., Fernández-Salas, J. A., Fraile, A., & Alemán, J. (2018). Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes. ACS catalysis, 8(3), 1884-1890. https://doi.org/10.1021/acscatal.7b03553
Esteban, Francisco, et al. "Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes." ACS catalysis vol. 8,3 (2018): 1884-1890. doi: https://doi.org/10.1021/acscatal.7b03553
Esteban F, Cieślik W, Arpa EM, Guerrero-Corella A, Díaz-Tendero S, Perles J, Fernández-Salas JA, Fraile A, Alemán J. Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes. ACS Catal. 2018 Mar 02;8(3):1884-1890. doi: 10.1021/acscatal.7b03553. Epub 2018 Jan 31. PMID: 29527400; PMCID: PMC5839603.
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ACS Catal. 2018 Mar 02;8(3):1884-1890. doi: 10.1021/acscatal.7b03553. Epub 2018 Jan 31.

Intramolecular Hydrogen Bond Activation: Thiourea-Organocatalyzed Enantioselective 1,3-Dipolar Cycloaddition of Salicylaldehyde-Derived Azomethine Ylides with Nitroalkenes.

ACS catalysis

Francisco Esteban, Wioleta Cieślik, Enrique M Arpa, Andrea Guerrero-Corella, Sergio Díaz-Tendero, Josefina Perles, José A Fernández-Salas, Alberto Fraile, José Alemán

Affiliations

  1. Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.
  2. Departamento de Química (Módulo 13), Facultad de Ciencias, Universidad Autónoma de Madrid, 28049 Madrid, Spain.
  3. Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, 28049 Madrid, Spain.
  4. Condensed Matter Physics Center (IFIMAC), Universidad Autónoma de Madrid, 28049 Madrid, Spain.
  5. X-Ray Diffraction Laboratory, Servicio Interdepartamental de Investigación, Universidad Autónoma de Madrid, 28049 Madrid, Spain.

PMID: 29527400 PMCID: PMC5839603 DOI: 10.1021/acscatal.7b03553

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

Conflict of interest statement

The authors declare no competing financial interest.

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