Asymmetric hydrogenation of phenylthio ketones with chiral Ru(II) catalysts

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 2951-2954

  Tranchier, Jean Philippe ^a   Ratovelomanana Vidal, Virginie ^a   Genêt, Jean Pierre ^a   Tong, Shaojing ^b   Cohen, Theodore ^b  

^a CNRS   (France)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ORGANOSULFUR DERIVATIVE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; HYDROGENATION; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030935322     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00530-3     Document Type: Article

References (27)

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4. The Chemistry of Sulfur-Containing Functional Groups; Patai, S., Rappoport, Z. Eds.; Wiley Interscience: New York, 1993. Oae, S. Organic Sulfur Chemistry; CRC Press: Boca Raton, 1991. Chemistry of Organosulfur Compounds; Belen'Kii, L. I., Ed.; Ellis Horwood: New York, 1990. See also Solladié, G. in Advances in Asymmetric Synthesis, G. R. Stephenson, Ed.; Chapman and Hall: London, 1996, pp 60-92.
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8. 3) e.e. 70%.
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11. Cohen, T.; Tong, S., manuscript in preparation.
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26. 2 (3.2 mg, commercially available from Acros), were placed in a Schlenk tube and purged three times with vacuum/argon and dissolved with 1 mL of acetone (degassed by 3 cycles of vacuum/argon at r.t). To this suspension was added 2.2 eq. of methanolic HBr (48% aq HBr in a methanolic solution) and the suspension was stirred at room temperature for 30 min. A yellow solid precipitated. The solvent was evaporated under vacuum and the phenylthio ketone (0.5 mM) dissolved in 2 mL of degassed MeOH was added to the Ru(II)-catalyst. The resulting mixture was placed under argon in a 250 mL stainless steel autoclave. The argon atmosphere was replaced by hydrogen by three cycles of pressurizing and the reaction was carried out until complete conversion.
27. Specific relationship between chiral atropoisomeric ligands (e.g. MeO-Biphep, 2-furyl-MeO-Biphep, Binap) and alcohol absolute configuration. equation presented L** = (S) configuration L* = (R) configuration of the biaryl ligand of the biaryl ligand equation presented intermediate n = 1,2 R = OMe ; R' = Ph MeO-Biphep R = OMe ; R' = furyl 2-furyl-MeO-Biphep