Catalytic asymmetric hydrogenation of aromatic ketones in room temperature ionic liquids

Tetrahedron Letters

Volumn 46, Issue 4, 2005, Pages 595-597

  Ngo, Helen L ^a   Hu, Aiguo ^a   Lin, Wenbin ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

Asymmetric catalysis; Hydrogenation; Ionic liquid

Indexed keywords

ALCOHOL; AROMATIC COMPOUND; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; RUTHENIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; HYDROGENATION; IMMOBILIZATION; LIQUID; ROOM TEMPERATURE;

EID: 11144299593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.150     Document Type: Article

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25. 1 (78 mg, 0.1 mmol) in anhydrous DMF (4 mL) was heated at 100°C under nitrogen for 1/2 h and was then cooled to rt for the addition of (R,R)-DPEN (21.5 mg, 0.1 mmol). With stirring, DPEN dissolved in ∼15 min and the color of solution slowly changed from orange-red to yellow. After stirring at 80°C for 2 h, solvent was removed under vacuum to give desired yellow solid of precatalyst, which was used for asymmetric hydrogenation reactions without further purification
26. 2 pressure was adjusted to 700 psi. After 24 h, the autoclave was depressurized and the reaction mixture was washed with 3.1 mL of hexane-IPA (30/1; v/v) three times. The organic solvent was removed under reduced pressure and the residue was passed through a mini silica gel column using diethyl ether as the eluent. An aliquot was analyzed on GC to give conversion and ee values
27. tBu, and IPA for another round of hydrogenation reaction