Evidence for a Boroxinate Based Brønsted Acid Derivative of VAPOL as the Active Catalyst in the Catalytic Asymmetric Aziridination Reaction
| Autor: | Li Huang, Gang Hu, William D. Wulff, Rui H. Huang |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Boron Compounds
Models Molecular chemistry.chemical_classification Magnetic Resonance Spectroscopy Chemistry Aziridines Imine General Chemistry Nuclear magnetic resonance spectroscopy Crystallography X-Ray Biochemistry Boroxine Article Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Ethyl diazoacetate Polymer chemistry Organic chemistry Counterion Brønsted–Lowry acid–base theory Derivative (chemistry) |
| Zdroj: | Journal of the American Chemical Society. 131:15615-15617 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/ja904589k |
| Popis: | Studies are described that were designed to determine the structure of the active catalyst in the asymmetric catalytic aziridination of imines with ethyl diazoacetate (AZ reaction). Evidence suggests that the active catalyst contains a boroxine ring in which one of the three boron atoms is spiro-fused with the two phenol groups of the VAPOL ligand. (11)B and (1)H NMR evidence supports the boroxinate structure B in which the counterion to the boroxinate is the protonated form of the imine. The boroxinate structure is also supported by two solid state structures of a VAPOL boroxinate in which the gegen cation is tetramethyl ammonium and 4-dimethylaminopyridinium. |
| Databáze: | OpenAIRE |
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