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Choubane H, Garrido-Castro AF, Alvarado C, et al. Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary. Chem Commun (Camb). 2018;54(27):3399-3402doi: 10.1039/C8CC01479E.
Choubane, H., Garrido-Castro, A. F., Alvarado, C., Martín-Somer, A., Guerrero-Corella, A., Daaou, M., Díaz-Tendero, S., Carmen Maestro, M., Fraile, A., & Alemán, J. (2018). Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary. Chemical communications (Cambridge, England), 54(27), 3399-3402. https://doi.org/10.1039/C8CC01479E
Choubane, Houcine, et al. "Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary." Chemical communications (Cambridge, England) vol. 54,27 (2018): 3399-3402. doi: https://doi.org/10.1039/C8CC01479E
Choubane H, Garrido-Castro AF, Alvarado C, Martín-Somer A, Guerrero-Corella A, Daaou M, Díaz-Tendero S, Carmen Maestro M, Fraile A, Alemán J. Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary. Chem Commun (Camb). 2018 Mar 29;54(27):3399-3402. doi: 10.1039/C8CC01479E. PMID: 29557452.
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Chem Commun (Camb). 2018 Mar 29;54(27):3399-3402. doi: 10.1039/C8CC01479E.

Intramolecular hydrogen-bond activation for the addition of nucleophilic imines: 2-hydroxybenzophenone as a chemical auxiliary.

Chemical communications (Cambridge, England)

Houcine Choubane, Alberto F Garrido-Castro, Cuauhtemoc Alvarado, Ana Martín-Somer, Andrea Guerrero-Corella, Mortada Daaou, Sergio Díaz-Tendero, M Carmen Maestro, Alberto Fraile, José Alemán

Affiliations

  1. Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain. [email protected] and L.S.P.B.E, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d'Oran- Mohamed Boudiaf, B. P 1505 El Mnaouer, Oran, 31000, Algeria.
  2. Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain. [email protected].
  3. Departamento de Química (Módulo 13), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain.
  4. L.S.P.B.E, Département de Chimie Organique Industrielle, Faculté de Chimie, Université des Sciences et de la Technologie d'Oran- Mohamed Boudiaf, B. P 1505 El Mnaouer, Oran, 31000, Algeria.
  5. Departamento de Química (Módulo 13), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain and Condensed Matter Physics Center (IFIMAC), Universidad Autónoma de Madrid, Madrid 28049, Spain and Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Madrid 28049, Spain.
  6. Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain. [email protected] and Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Madrid 28049, Spain.

PMID: 29557452 DOI: 10.1039/C8CC01479E

Abstract

The addition of nucleophilic imines, using 2-hydroxybenzophenone as a chemical auxiliary, is presented. An intramolecular six-membered ring via hydrogen bonding that enhances the reactivity and selectivity is the key of this strategy, which is supported by DFT calculations and experimental trials.

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