新型双功能手性硫脲小分子催化剂的合成及其在Michael加成反应中的应用

Synthesis of New Bifunctional Chiral Thioureas Organocatalysts and Their Application in Michael Addition

奎宁和手性氨基醇通过硫脲片段组合,合成了4个新型的具有多氢键供体的双功能手性硫脲类小分子催化剂(5a～5d),其结构经1H NMR,13C NMR,IR和HR-MS表征。以查尔酮为底物,硝基甲烷为亲核试剂,考察了5a～5d在Michael加成反应中的催化活性和对映选择性。结果表明,以Na2CO3为碱,三氯甲烷为溶剂,5c为催化剂,于室温反应24 h,加成产物4-硝基-1,3-二苯基丁烷-1-酮的收率69%,对映选择性86%。

Four new chiral thiourea bifunctional organocatalysts（5a - 5d） were synthesized by the re- action of quinine with chiral β-amino alcohol. The structures were characterized by I H NMR, 13C NMR, IR and HR-MS. The catalytic performance and selectivity of 5a - 5d were investigated by the Michael addition between chalcone and nitromethane. The results showed that the yield was 69% with 86%e. e. of 4-nitro-1,3-diphenylbutan-1-one） （addition product） using Na2CO3 as the alkali, chloroform as the solvent and 5c as the catalyst at room temperature for 24 h.