In this master’s thesis, the research was focused on the application of pyrrolinone derivatives in asymmetric transformations. Enantioselective synthesis was achieved with the application of chiral noncovalent bifunctional organocatalysts. This work covers the preparation of a library of racemic compounds, that were used for the optimization of chiral HPLC method for the separation of enantiomers and subsequently for the determination of enantiomeric excess of the corresponding enantiomerically enriched compounds. In the first part, [4+2] annulation of N-unsubstituted arylidene-Δ2-pyrrolin-4-ones with malononitrile were examined, which resulted in nonracemic dihydropyrano[3,2-b]pyrrole derivatives. The determination of enantiomeric excess of chiral nonracemic compounds, done by chiral HPLC method, was accompanied with numerous factors, that must be put into the consideration, to be able to obtain accurate enantioselectivity results. In the following research, tetramic acids derivatives were applied in organocatalyzed reactions. 1,4-addition of tetramic acids to trans-β-nitrostyrene derivatives resulted in a chiral center formation as new C–C bond was formed. A small library of O-alkylated adducts of tetramic acids and trans-β-nitrostyrene derivatives was synthesized. A chiral nonracemic N-Gly-Boc substituted tetramic acid derivative was used for the selected follow-up modifications. With the implementation of orthogonal protection and peptide chemistry, macrocyclic product containing pyrrolin-2-one heterocycle was synthesized.
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