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EnglishThe simple tetraminocalix[4]arene 1, which contains weak H-bond-donor NH2 groups, is reported to be a highly efficient organocatalyst for the Vinylogous Mukaiyama Aldol Reaction (VMAR) of 2-(trimethylsilyloxy)furan 5 with α-ketoesters 6 a-l under "on-water" conditions owing to the hydrophobic amplification of weak H-bond interactions. The catalytic efficiency of calixarene catalyst 1 was shown to be closely related to its recognition abilities towards the reactants 5 and 6 through a multipoint recognition model. The proposed model provided good explanations for the differences on the reaction rate acceleration and on the stereoselectivity observed with different substrates.
| Titolo: | A Simple Tetraminocalix[4]arene as a Highly Efficient Catalyst under "On-Water" Conditions through Hydrophobic Amplification of Weak Hydrogen Bonds |
| Autori: | |
| Data di pubblicazione: | 2017 |
| Stato di pubblicazione: | Pubblicato |
| Rivista: | |
| Abstract: | The simple tetraminocalix[4]arene 1, which contains weak H-bond-donor NH2 groups, is reported to be a highly efficient organocatalyst for the Vinylogous Mukaiyama Aldol Reaction (VMAR) of 2-(trimethylsilyloxy)furan 5 with α-ketoesters 6 a-l under "on-water" conditions owing to the hydrophobic amplification of weak H-bond interactions. The catalytic efficiency of calixarene catalyst 1 was shown to be closely related to its recognition abilities towards the reactants 5 and 6 through a multipoint recognition model. The proposed model provided good explanations for the differences on the reaction rate acceleration and on the stereoselectivity observed with different substrates. |
| Handle: | http://hdl.handle.net/11368/2901845 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/chem.201701247 |
| URL: | http://onlinelibrary.wiley.com/doi/10.1002/chem.201701247/abstract |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| De-Rosa_et_al-2017-Chemistry_-_A_European_Journal.pdf | Documento in Versione Editoriale | Digital Rights Management non definito | Administrator Richiedi una copia | |
| 3904_11368_2901845_EUT.pdf | Bozza finale post-referaggio (post-print) | Digital Rights Management non definito | Open Access Visualizza/Apri |
