Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation

Tetrahedron Letters

Volumn 44, Issue 50, 2003, Pages 9025-9028

  Gergely, Ildikó ^a   Hegedüs, Csaba ^b   Szöllosy, Áron ^c   Monsees, Axel ^d   Riermeier, Thomas ^d   Bakos, József ^a  

^a UNIVERSITY OF PANNONIA   (Hungary)

^b INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^c BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^d EVONIK INDUSTRIES AG   (Germany)

Author keywords

Asymmetric hydrogenation; Dimethyl itaconate; Diphosphinites; Methyl(Z) acetamido cinnamate; Rhodium

Indexed keywords

CINNAMIC ACID DERIVATIVE; ITACONIC ACID; NAPHTHOL DERIVATIVE; RHODIUM DERIVATIVE; RHODIUM DIPHOSPHINITE; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; ENANTIOSELECTIVITY; HYDROGENATION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOSPECIFICITY;

EID: 0242458442     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.217     Document Type: Article

References (21)

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19. 1J(P,Rh)=166.2 Hz).
20. 2 and then shaken at a frequency of 180/min, 75° from the upright position, with horizontal amplitude of 3 centimeters. The reaction was monitored by the change in pressure. The reaction mixture and the distilled products were analyzed by gas chromatography. The enantiomeric excess of the product (2) was determined by GC analysis of the distilled product (Hewlett-Packard HP 4890 gas chromatograph, split/spitless injector, β-DEX 225, 30 m, internal diameter 0.25 mm, film thickness 0.25 μm, carrier gas: 100 kPa nitrogen, F.I.D. detector; the retention times of the enantiomers are 30.5 min (R), 32.1 min (S)). In the case of 6 the reaction mixture was passed through a short silicagel column to remove the catalyst. The enantiomeric excess was determined on CP-CHIRASIL-L-VAL column (25 m, internal diameter 0.25 mm, film thickness 0.12 μm, carrier gas: 100 kPa nitrogen, F.I.D. detector; the retention times of the enantiomers are 32.5 min (R), 34.2 min (S)). The configuration of the prevailing enantiomer in the products was determined by the sign of optical rotation of the hydrogenated product. Conversions were determined by GC (SPB-1).
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