This study reports the enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. The catalysts were synthesized by reacting 3,5-bis(trifluoromethyl)phenyl isothiocyanate with (R,R)-N,N-dimethyl-trans-diaminocyclohexane under an argon atmosphere. The resulting thioureas were characterized by NMR, IR, and mass spectrometry. The Michael addition was carried out using trans-β-nitrostyrene and diethyl malonate in the presence of the thiourea catalyst. The reaction was monitored by chiral HPLC, and the enantiomeric excess (ee) was determined. The products were isolated by preparative TLC and characterized by NMR, IR, and mass spectrometry. The results showed high enantioselectivity, with ee values ranging from 81% to 93%. The study demonstrates the effectiveness of bifunctional organocatalysts in achieving high enantioselectivity in the Michael addition of malonates to nitroolefins. The catalysts were effective for a variety of substrates, including different substituted nitroolefins and malonates. The study provides a detailed characterization of the catalysts and products, as well as the reaction conditions that lead to high enantioselectivity. The results suggest that the bifunctional organocatalysts are a promising approach for the enantioselective Michael addition of malonates to nitroolefins.This study reports the enantioselective Michael reaction of malonates to nitroolefins catalyzed by bifunctional organocatalysts. The catalysts were synthesized by reacting 3,5-bis(trifluoromethyl)phenyl isothiocyanate with (R,R)-N,N-dimethyl-trans-diaminocyclohexane under an argon atmosphere. The resulting thioureas were characterized by NMR, IR, and mass spectrometry. The Michael addition was carried out using trans-β-nitrostyrene and diethyl malonate in the presence of the thiourea catalyst. The reaction was monitored by chiral HPLC, and the enantiomeric excess (ee) was determined. The products were isolated by preparative TLC and characterized by NMR, IR, and mass spectrometry. The results showed high enantioselectivity, with ee values ranging from 81% to 93%. The study demonstrates the effectiveness of bifunctional organocatalysts in achieving high enantioselectivity in the Michael addition of malonates to nitroolefins. The catalysts were effective for a variety of substrates, including different substituted nitroolefins and malonates. The study provides a detailed characterization of the catalysts and products, as well as the reaction conditions that lead to high enantioselectivity. The results suggest that the bifunctional organocatalysts are a promising approach for the enantioselective Michael addition of malonates to nitroolefins.