Metal(salen) Complex Catalysed, Asymmetric Synthesis of (S)-2-hydroxy- (3-Phenoxyphenyl)acetonitrile Derivatives
Michael North and James Watson
Affiliation: School of Chemistry and University Research Centre in Catalysis and Intensified Processing, Newcastle University, Bedson Building, Newcastle upon Tyne, NE1 7RU, England, UK
Keywords: Asymmetric, cyanohydrin, insecticide, pyrethroid, salen, titanium, vanadium.
The synthesis of (S)-2-hydroxy-(3-phenoxyphenyl)acetonitrile derivatives (components of pyrethroid insecticides)
by the asymmetric addition of three different cyanide sources to 3-phenoxybenzaldehyde is investigated. Titanium
and vanadium(salen) complexes are used as asymmetric catalysts and the processes are analyzed on the basis of both degree
of asymmetric induction and relative cost to determine the commercially most viable synthesis. This provides a
greener route to pyrethroid insecticides since the enantiomers of synthetic pyrethroids have different insecticidal activity,
toxicity and environmental persistence. Thus, by producing only the stereoisomer with the most desirable properties, the
production of waste and material with inferior effects on biological organisms and the environment can be avoided.
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