Synthesis of enantiopure 1,2-diamine attached to cross-linked polystyrene and its application to an insoluble catalyst for asymmetric hydrogenation

Tetrahedron Letters

Volumn 44, Issue 19, 2003, Pages 3825-3828

  Itsuno, Shinichi ^a   Tsuji, Atsushi ^a   Takahashi, Miyuki ^a  

^a TOYOHASHI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

1,2 diamine; Asymmetric hydrogenation; Cross linked polystyrene

Indexed keywords

1,2 DIAMINE; ACETOPHENONE; BENZYL ETHER; DIAMINE DERIVATIVE; ETHER DERIVATIVE; HYDROXYL GROUP; LIGAND; PHENOL; POLYSTYRENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL PARAMETERS; CHIRALITY; CROSS LINKING; HYDROGENATION; METHYLATION; SOLUBILITY; SYNTHESIS;

EID: 0037420809     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00742-1     Document Type: Article

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24. n (23 mg, 0.025 mmol) were added to dry DMF (2 mL) in a dry, degassed 100-mL glass autoclave. To this suspension was added a degassed mixture of acetophenone (0.58 mL, 5 mmol) and a 1.0 M 2-propanol solution of t-BuOK (100 μL, 0.1 mmol) in 2-propanol (2 mL), and then, hydrogen was pressurized to 1 MPa. The suspension was stirred at room temperature for 1 h. After the reaction, the mixture was filtered and concentrated. The yield determined by GC was 100%. The enantioselectivity was determined by HPLC analysis using a Daicel Chiralcel OD column (eluent, 1:20 2-propanol-hexane; flow rate, 0.4 mL/min).
25. 2.
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