1984 Volume 57 Issue 6 Pages 1570-1575
The enantiomer-differentiating acylation (kinetic resolution) of 1-phenylalkylamines and their derivatives was carried out with (S)-2-phenylbutyric anhydride and its derivatives in aqueous and nonaqueous media. On the basis of the distributions of the two diastereomeric products, the molecular interactions between hydrocarbon residues responsible for the structural recognition of the reacting molecules were studied. In nonpolar media, the (R,S)-isomer was predominantly formed over the (S,S)-isomer. Moreover, the differentiation was mainly controlled by the size of the alkyl substituents of the substrates. In aqueous media, though, the (S,S)-isomer was predominantly formed. By a comparative study of the cyclohexyl analogs of the substrates and the reagents, it was shown that alkyl-phenyl and/or phenyl-phenyl interactions were important in the recognition process. A partitioning process of the substrate into the reagent phase was not effective in the differentiation of the enantiomer by the reaction in suspensions of optically active reagents in highly aqueous media.
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