Rénio Márcia, Murtinho Dina, Ventura M Rita
Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Oeiras, Portugal.
Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, Coimbra, Portugal.
Chirality. 2022 May;34(5):782-795. doi: 10.1002/chir.23424. Epub 2022 Feb 15.
Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were synthesized from (+)-camphoric acid. These catalysts were easily obtained in up to two to five synthetic steps, in a flexible approach that facilitates their structure variation. Their catalytic activity was examined in the asymmetric Michael addition of 1,3-dicarbonyl compounds to several trans-β-nitrostyrenes. Yields up to 98% and enantiomeric excesses up to 74% and high diastereoselectivities when applicable (dr up to 93:7) were obtained in these reactions showing that 1,3-diamine-derived bifunctional thioureas are efficient organocatalysts.
新型1,3 - 二胺衍生的双功能硫脲和方酰胺有机催化剂由（+）-樟脑酸合成。这些催化剂通过多达两到五步的合成步骤即可轻松获得，采用灵活的方法，便于其结构变化。在1,3 - 二羰基化合物与几种反式β-硝基苯乙烯的不对称迈克尔加成反应中考察了它们的催化活性。在这些反应中，产率高达98%，对映体过量高达74%，并且在适用时具有高非对映选择性（非对映体比例高达93:7），表明1,3 - 二胺衍生的双功能硫脲是有效的有机催化剂。
