Ozgun Ummu, Genc Hayriye Nevin
Department of Chemistry, A. K. Education Faculty, Necmettin Erbakan University, Konya, Türkiye.
Faculty of Engineering, Necmettin Erbakan University, Konya, Türkiye.
Chirality. 2024 Sep;36(9):e23711. doi: 10.1002/chir.23711.
Novel chiral tetraaza-bridged calix[4]arene[2]triazine-based organocatalysts were synthesized and used for catalytic asymmetric Michael reaction of acetylacetone to various aromatic nitrostyrenes. Chiral subunits (R)- and (S)-1,2,3,4-tetrahydro-1-naphthylamine were attached to the tetraaza-bridged calix[4]arene[2]triazine platform in both enantiomeric forms. The R configuration of the major enantiomer of the Michael product was obtained when 3a was used as catalyst, and the S configuration was obtained when 3b was used as catalyst. This indicated that the configuration of the Michael product was controlled by the chiral calixarene moiety. The Michael adducts were obtained in excellent yields (91%) and enantioselectivities (98%).
合成了新型手性四氮杂桥联杯[4]芳烃[2]三嗪基有机催化剂，并将其用于催化乙酰丙酮与各种芳香族硝基苯乙烯的不对称迈克尔反应。手性亚基（R）-和（S）-1,2,3,4-四氢-1-萘胺以两种对映体形式连接到四氮杂桥联杯[4]芳烃[2]三嗪平台上。当使用3a作为催化剂时，迈克尔产物的主要对映体为R构型；当使用3b作为催化剂时，得到S构型。这表明迈克尔产物的构型由手性杯芳烃部分控制。迈克尔加合物的产率极高（91%），对映选择性也很高（98%）。
