Stereochemical control of the interfacial darzens condensation

Abstract
The condensation of α-chlorophenylacetonitrile (1) with benzaldehyde (2) carried out in the presence of 50% aq. NaOH and a quaternary ammonium catalyst gives trans-2,3-diphenylglycidonitrile, while without the catalyst, the cis-isomer predominates; in the latter case the reaction proceeds at the interface.

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