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Mechanistic comparison of aluminium based catalysts for asymmetric cyanohydrin synthesis

Lookup NU author(s): Professor Michael North, Dr Pedro Villuendas, Courtney Williamson

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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. (C) 2010 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): North M, Villuendas P, Williamson C

Publication type: Article

Publication status: Published

Journal: Tetrahedron

Year: 2010

Volume: 66

Issue: 10

Pages: 1915-1924

Print publication date: 11/01/2010

Date deposited: 22/06/2010

ISSN (print): 0040-4020

ISSN (electronic): 1464-5416

Publisher: Pergamon

URL: http://dx.doi.org/10.1016/j.tet.2010.01.004

DOI: 10.1016/j.tet.2010.01.004

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