手性叔胺脲催化靛红亚胺与苯胺的不对称aza-Mannich反应

Chiral tertiary amine urea catalyzed enantioselective sza-Mannich reaction of isatin ketimines and aryl amines

报道了Takemoto型手性(硫)脲催化靛红亚胺与苯胺的不对称aza-Mannich反应。在0.1 mmol反应量下,筛选出最佳催化剂体系为:10 mol%催化剂N-[3,5-二(三氟甲基)苯基]-N′-[(1S,2S)-2-(二甲氨基)环己基]脲1d,1 mL乙醚,0℃反应。以71~82%的收率和最高达97%ee获得系列手性3-N,N′-靛红缩酮。

Takemoto􀆳s(thio)urea derivatives were applied in the asymmetric aza-Mannich reaction of isatin ketimines and aryl amines.Under 0.1 mmol ammount,the optimal conditions were screened to be 10 mol%loading catalyst N-[3,5-Bis(trifluoromethyl)phenyl]-N′-[(1S,2S)-2-(dimethylamino)cyclohexyl]urea 1d in Et_(2)O(1 mL)at 0℃.Different substrates were evaluated for the generality of this reaction,and the desired chiral 3-N,N′-ketal isatins were obtained in 71~82%yields with up to 97%enantiomeric excess(ee).