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Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation
| Content Provider | Semantic Scholar |
|---|---|
| Author | Wiedenhoeft, Dennis Benoit, Adam Wu, Yibiao Porter, Jacob D. Meyle, Elisia Yeung, Teresa H. W. Huff, Raechel Lindeman, Sergey V. Dockendorff, Chris |
| Copyright Year | 2016 |
| Abstract | Abstract Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalysts were prepared in several steps from amino acid starting materials, and these were combined with a variety of metal Lewis acids for potential use as catalysts for various carbon–carbon bond formations. Air- and moisture-tolerant catalysts for enantioselective direct aldol reactions with activated benzaldehyde acceptors were identified, with optimal results obtained with proline-derived oxazole–carboxamide precatalysts combined with Zn(OTf)2 or lanthanide (III) salts. Control studies support the hypothesis that these act as unimolecular hybrid catalysts for the aldol reaction of propionaldehyde and 4-nitrobenzaldehyde. |
| Starting Page | 3905 |
| Ending Page | 3916 |
| Page Count | 12 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/j.tet.2016.05.014 |
| Volume Number | 72 |
| Alternate Webpage(s) | https://epublications.marquette.edu/cgi/viewcontent.cgi?article=1573&context=chem_fac&httpsredir=1&referer= |
| Alternate Webpage(s) | https://doi.org/10.1016/j.tet.2016.05.014 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
