Direct asymmetric α-amination of aldehydes with azodicarboxylates in ionic liquids catalyzed by imidazolium ion-tagged proline organocatalyst

Tetrahedron Letters

Volumn 51, Issue 47, 2010, Pages 6105-6107

  Ding, Xiong ^a   Jiang, Hong Lai ^a   Zhu, Cheng Jian ^a,b   Cheng, Yi Xiang ^a  

^a NANJING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Amination; Aldehydes; Asymmetric organocatalysis; Ionic liquids; Recyclability

Indexed keywords

ALDEHYDE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; IMIDAZOLE; IONIC LIQUID; PROLINE;

AMINATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; REACTION ANALYSIS; REACTION TIME;

EID: 77958451139     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.036     Document Type: Article

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62. 4]: To a test-tube equipped with a magnetic stirring bar and charged with ionic liquid (1.5 mL) was added catalyst 1 (10 mol %) and aldehyde (0.5 mmol). The mixture was stirred for 2 min at 0 °C followed by addition of azodicarboxylates (0.25 mmol). The resulting solution was then stirred until the yellow color of the mixture disappeared and the completion of amination reaction was determined by TLC. The reaction mixture was then extracted with ethyl ether (6 × 5 mL) followed by solvent evaporation using a rotary evaporator. To the crude α-hydrazine aldehyde intermediate was added methanol (2 mL). The mixture was cooled to 0 °C and sodium borohydride (0.55 mmol) was added. After 5 min, the reaction was quenched with saturated aqueous ammonium chloride solution (0.5 mL) and the resulting mixture was extracted with ethyl acetate (4 × 3 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated under vacuum after filtration. Purification by column chromatography on silica gel (ethyl acetate/petroleum ether, 1:3-1:10) gave pure α-aminated products as white solids.
63. 4 (1.5 mL) were stirred for 20 min at 0 °C and then extracted with ethyl ether (6 × 5 mL). The residue was dried under vacuum for about 60 min at 60 °C, and reused for the next run of reaction. This procedure could be repeated for four times at least.