Journal
TETRAHEDRON
Volume 66, Issue 10, Pages 1915-1924Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.01.004
Keywords
Aluminium; Cyanohydrin; Kinetics; Phosphine oxide; Lewis acid; Lewis base
Categories
Funding
- Engineering and Physical Sciences Research Council [EP/E01819X/1] Funding Source: researchfish
- EPSRC [EP/E01819X/1] Funding Source: UKRI
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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. (C) 2010 Elsevier Ltd. All rights reserved.
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