Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis |
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Authors: | Michael North Pedro Villuendas Courtney Williamson |
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Affiliation: | School of Chemistry and University Research Centre in Catalysis and Intensified Processing, Bedson Building, Newcastle University, Newcastle upon Tyne. NE1 7RU, UK |
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Abstract: | A kinetic analysis of the asymmetric addition of trimethylsilyl cyanide to benzaldehyde using three aluminium based catalysts has been carried out. All three catalysts displayed rate equations, which were first order in trimethylsilyl cyanide concentration and zero order in benzaldehyde concentration. The results are consistent with a common mechanism for effective asymmetric catalysis of cyanohydrin synthesis, involving combined activation of the aldehyde by a Lewis acid and activation of the trimethylsilyl cyanide by a Lewis base. The mechanistic analysis was also applied to a magnesium-based catalyst system to demonstrate its general applicability. |
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Keywords: | Aluminium Cyanohydrin Kinetics Phosphine oxide Lewis acid Lewis base |
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