engleski

New chiral stationary phases containing N-(1-arylpropyl)-3, 5-dinitrobenzamide selector

Based on our prior work in Laboratory for Stereoselective Catalysis and Biocatalysis at Ruđer Bošković Institute in the field of chiral recognition of Pirkle-type chiral stationary phases (CSPs) [1-4] we designed and prepared the new sort of CSPs. To improve the chiral discrimination performance these new Pirkle-type CSPs have lacking some of non-stereoselective adsorption sites. Chiral selector of CSP I, an N-(1-arylpropyl)-3, 5-dinitrobenzamide unit, possesses all the characteristics of a good selector – it is rigid and contains a strong pi-accepting 3, 5-dinitrobenzoyl (DNB), and a strong pi-donating aromatic group (Ar). The necessary compounds were prepared from enantiomerically pure allyl-arylamines (I) obtained by enzymatic resolution or preparative chiral chromatography of racemic amines. Previous synthetic step was [3, 3]-sigmatropic rearrangement of acyclic imidates that gives racemic amines. Imidates are easily prepared from corresponding alcohols which are usually commercially unavailable and must be synthesized from commercial aryl aldehydes.

chiral stationary phases; Pirkle type; enantioseparation; enzymatic resolution

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