Issue 27, 2018
From the journal:

Chemical Communications

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

Houcine Choubane,ab   Alberto F. Garrido-Castro, ORCID logo a   Cuauhtemoc Alvarado,a   Ana Martín-Somer, ORCID logo c   Andrea Guerrero-Corella, ORCID logo a   Mortada Daaou,b   Sergio Díaz-Tendero, ORCID logo cde   M. Carmen Maestro, ORCID logo a   Alberto Fraile ORCID logo ae  and  José Alemán ORCID logo *ae  

* Corresponding authors

a Departamento de Química Orgánica (Módulo 1), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain
E-mail: jose.aleman@uam.es
Web: http://www.uam.es/jose.aleman

b 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, Algeria

c Departamento de Química (Módulo 13), Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid 28049, Spain

d Condensed Matter Physics Center (IFIMAC), Universidad Autónoma de Madrid, Madrid 28049, Spain

e Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid, Madrid 28049, Spain

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.

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

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Article information

DOI
https://doi.org/10.1039/C8CC01479E
Article type
Communication
Submitted
21 Feb 2018
Accepted
09 Mar 2018
First published
09 Mar 2018

Chem. Commun., 2018,54, 3399-3402

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

H. Choubane, A. F. Garrido-Castro, C. Alvarado, A. Martín-Somer, A. Guerrero-Corella, M. Daaou, S. Díaz-Tendero, M. Carmen Maestro, A. Fraile and J. Alemán, Chem. Commun., 2018, 54, 3399 DOI: 10.1039/C8CC01479E

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