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

Author
Choubane, Houcine; Garrido-Castro, Alberto F.; Alvarado, Cuauhtemoc; Martín-Somer, Ana; Guerrero-Corella, Andrea; Daaou, Mortada; Díaz-Tendero Victoria, Sergiountranslated; Carmen Maestro, M.; Fraile Carrasco, Albertountranslated; Alemán Lara, José Juliánuntranslated
Entity
UAM. Departamento de Química Orgánica
Publisher
Royal Society of Chemistry
Date
2018-03-09
Citation
Chemical Communications 54.27(2018): 3399-3402
ISSN
1359-7345
DOI
10.1039/c8cc01479e
Funded by
Spanish Government (CTQ2015-64561-R, CTQ2016-76061-P, and MDM-2014-0377), Prodep (UJAT-PTC-247) and CCC-UAM are acknowledged. A. G. thanks MINECO for a PhD fellowship (FPI) and A. M. S. thanks CAM for a postdoctoral contract (2016-T2/IND-1660)
Project
Gobierno de España. CTQ2015-64561-R; Gobierno de España. CTQ2016-76061-P; Gobierno de España. MDM-2014-0377
Editor's Version
https://doi.org/10.1039/c8cc01479e
Subjects
Enantioselectivity; Aldehydes; Direct aldo; Química
URI
http://hdl.handle.net/10486/687103
Rights
© 2018 The Royal Society of Chemistry

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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Google™ Scholar:Choubane, Houcine - Garrido-Castro, Alberto F. - Alvarado, Cuauhtemoc - Martín-Somer, Ana - Guerrero-Corella, Andrea - Daaou, Mortada - Díaz-Tendero Victoria, Sergio - Carmen Maestro, M. - Fraile Carrasco, Alberto - Alemán Lara, José Julián

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