Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis

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.