The effect of the substrate structure on the stereoselectivity in an asymmetric hydrogenation of unsaturated carboxylic acids over cinchonidine-modified palladium catalyst

Tetrahedron Asymmetry

Volumn 16, Issue 9, 2005, Pages 1573-1575

  Sugimura, Takashi ^a   Watanabe, Junya ^a   Okuyama, Tadashi ^a   Nitta, Yuriko ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 17844408672     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.03.020     Document Type: Article

References (15)

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2. H.U. Blaser, H.P. Jallet, M. Müller, and M. Studer Catal. Today 37 1997 441
3. P.B. Wells, and A.G. Wilkinson Top. Catal. 5 1998 39
4. W.R. Huck, T. Mallat, and A. Baiker Catal. Lett. 80 2002 87
5. Y. Nitta, and K. Kobiro Chem. Lett. 1996 897
6. Y. Nitta Chem. Lett. 1999 635
7. Y. Nitta, and Y. Okamoto Chem. Lett. 1998 1115
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9. Y. Nitta, and A. Shibata Chem. Lett. 1998 161
10. J.R. Johnson Org. React. 1 1942 210
11. The hydrogenation was carried out in a magnetically stirred 50 mL glass reactor at room temperature (22-24°C) under an atmospheric pressure of hydrogen. The catalyst (0.02 g) and cinchonidine (0.02 mmol) were pre-reduced by stirring for 30 min in 10 mL of 1,4-dioxane containing 2.5% (v/v) of water. Then 0.5 mmol of a substrate was introduced to the mixture. Benzylamine (0.6 equiv) was further added when necessary
12. The dihedral angles for 1 and its conjugate base calculated at the AM-1 level are 78.1° and 86.3°, respectively
13. Absolute stereochemistries of the new compounds obtained by the hydrogenation of 2-4 are assigned as S by their CD spectra
14. The addition of benzylamine prior to the substrate introduction causes a considerable decrease in the product ee, which suggests that cinchonidine is partly desorbed from Pd surface as a result of competitive adsorption of benzylamine
15. 2 and a nonporous titania (JRC-TIO-3, Catalysis Society of Japan) and by heating in a hydrogen flow at 473 K for 1 h immediately before use according to the procedure described previously. Y. Nitta, T. Kubota, and Y. Okamoto Bull. Chem. Soc. Jpn. 73 2000 2635