Enantioselective hydrogenation of itaconate using rhodium bihelicenol phosphite complex. Matched/mismatched phenomena between helical and axial chirality

Tetrahedron Letters

Volumn 44, Issue 27, 2003, Pages 4969-4971

  Nakano, Daisuke ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ITACONIC ACID; LIGAND; MENTHOL; PHOSPHINE DERIVATIVE; PHOSPHITE; RHODIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; ENANTIOSELECTIVITY; HYDROGENATION; ISOMERISM; PURIFICATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 0037842936     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01183-3     Document Type: Article

References (10)

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4. Claver C., Fernandez E., Gillon A., Heslop K., Hyett D.J., Martorell A., Orpen A.G., Pringle P.G. Chem. Commun. 2000;961.
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7. Vanden Berg M., Minnaard A.J., Schudde E.P., Van Esch J., De Vries A.H.M., De Vries J.G., Feringa B.L. J. Am. Chem. Soc. 122:2000;11539.
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9. Brunel J.-M., Buono G. J. Org. Chem. 58:1993;7313.
10. 4 (4.0 mg, 0.01 mmol) and (M,M,S,l)-2 (24 mg, 0.03 mmol) were added to degassed dichloromethane (5 mL), and the orange solution was stirred at room temperature for 5 min. In a stainless autoclave (50 mL) was added dimethyl itaconate 4 (158 mg, 1 mmol). An argon atmosphere was applied, and degassed dichloromethane (5 mL) was added. The rhodium complex solution was then added to the substrate solution in the autoclave, and the mixture was stirred for 1 min. Then, the solution was cooled to -78°C, and 90 atm of hydrogen was applied. The mixture was stirred for 6 h, and warmed to room temperature for 18 h. The gas was removed, and the solvents were evaporated under reduced pressure. After short silica gel column chromatography, bulb-to-bulb distillation gave (S)-5 (158 mg, quant., 96% ee) as colorless oil.