Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry.
Trabajo presentado en el 6th ORCA Meeting (Cost Action on organocatalysis) celebrado en Palermo (Italia) del 07 al 10 de mayo de 2014.
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2014-05-07
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| Online Access: | http://hdl.handle.net/10261/180533 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 |
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dig-ipna-es-10261-1805332019-04-26T00:58:00Z Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. Cruz-Acosta, Fabio Armas, Pedro de García-Tellado, Fernando Ministerio de Ciencia e Innovación (España) European Commission Consejo Superior de Investigaciones Científicas (España) Trabajo presentado en el 6th ORCA Meeting (Cost Action on organocatalysis) celebrado en Palermo (Italia) del 07 al 10 de mayo de 2014. In this communication we described the development and implementation of the first example of a hydrogen bond based organocatalytic multicomponent manifold operating “in the presence of water” conditions. The manifold performs a multicomponent and stereoselective version of the organocatalyzed aza-Henry reaction and it utilizes aniline, aromatic or aliphatic aldehydes, primary or secondary nitroalkanes, N,N-dimethylcyclohexylamine as the catalytic base and a chiral thiourea or squaramide catalyst as the chiral source to afford the corresponding -disubstituted -nitroamine derivatives. The reaction does not require a large excess of nitroalkane (two equivalents are enough) to afford the corresponding product in good yield and high stereoselectivity (up to ≥99.5:0.5 e.r. and ≥99.5:0.5 d.r., anti-adduct). The catalysis is performed through H-bond interactions between the nitroalkane and the chiral catalyst in the presence of interfacial water. Importantly, each family of catalysts delivers the -nitroamine product with complementary enantioselectivity, allowing for the selective access to the two enantiomeric series of these building blocks in an efficient, instrumentally simple and scalable manner. 2019-04-25T09:33:12Z 2019-04-25T09:33:12Z 2014-05-07 2019-04-25T09:33:12Z 6th ORCA Meeting (Cost Action on organocatalysis) http://hdl.handle.net/10261/180533 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 open |
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Trabajo presentado en el 6th ORCA Meeting (Cost Action on organocatalysis) celebrado en Palermo (Italia) del 07 al 10 de mayo de 2014. |
| author2 |
Ministerio de Ciencia e Innovación (España) |
| author_facet |
Ministerio de Ciencia e Innovación (España) Cruz-Acosta, Fabio Armas, Pedro de García-Tellado, Fernando |
| author |
Cruz-Acosta, Fabio Armas, Pedro de García-Tellado, Fernando |
| spellingShingle |
Cruz-Acosta, Fabio Armas, Pedro de García-Tellado, Fernando Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| author_sort |
Cruz-Acosta, Fabio |
| title |
Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| title_short |
Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| title_full |
Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| title_fullStr |
Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| title_full_unstemmed |
Water-Compatible Hydrogen-Bond Activation: A Scalable and Organocatalytic Model for the Stereoselective Multicomponent Aza-Henry. |
| title_sort |
water-compatible hydrogen-bond activation: a scalable and organocatalytic model for the stereoselective multicomponent aza-henry. |
| publishDate |
2014-05-07 |
| url |
http://hdl.handle.net/10261/180533 http://dx.doi.org/10.13039/501100004837 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003339 |
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