The dissertation is devoted to the development of methods for the synthesis of five-membered cyclic compounds of high enantiomeric purity using enzymatic deracemization: cyclopentanols, 2,3-dihydro-1H-indenols, pyrrolidines, tetrahydrofurans and their derivatives. Due to the analysis of literature data on the application of methods of biocatalytic trans-esterification of racemates, this method is the best tool for obtaining the abovementioned synthetic blocks with a high degree of enantiomeric excess. This direction has been the main focus of the presented work. Particular attention in the scientific space is paid to the development of methods for obtaining chiral compounds of high stereochemical purity, which are potentially biologically active or can be used as starting materials for the synthesis of biologically or pharmacologically active compounds. The main aim of the proposed project is to develop methods for the enzymatic production of chiral compounds with potential biological or pharmacologycal activity, which can be used as starting reagents in the synthesis of biologically active substances. In this work methods were developed that make it possible to synthesize chiral compounds of high enantiomeric purity, also chiral synthetic blocks (synthons) of important biologically active compounds were obtained and their properties were studied. It is the convergent method based on the combined use of enzymatic analysis and chiral HPLC that was first introduced in this dissertation. This method allows increasing the accuracy of determining the absolute configurations of 2,3-dihydro-1H-indenols. The results of the convergent determinations of the absolute configuration completely coincide, which indicates the reliability of the proposed technique and its suitability for routine work with five-membered secondary alcohols. As a result, the absolute configurations of a number of 2,3-dihydro-1H-indenols were determined and the errors in the absolute configurations described in the chemical literature were corrected. It was proven that (S)-alcohols are better retained by the chiral stationary phase when using a Chiralcell chiral column, and therefore, the alcohol having the (R)-configuration is eluted first. This is because the (S)-secondary alcohol forms a strong hydrogen bond with the chiral sugar contained in the stationary phase. The practical significance of the obtained results lies in the development of a preparatively convenient biocatalytic enantioselective method for the synthesis of chiral cycloalkanols and 2,3-dihydro-1H-indenols and creation of highly effective approaches to the preparation of chiral five-membered cyclic synthons based on them, namely, cyclopentanol derivatives, halo-2,3-dehydro-1H-indenols, 2,3-dihydro-1H-indenediols, pyrrolidinols, tetrahydrofuranols, as well as development of new enantioselective approaches to the synthesis of 4-fluoroalkylpyrrolidines.
