873841-97-5Relevant academic research and scientific papers
Enantiomeric products formed via different mechanisms: asymmetric hydrogenation of an α,β-unsaturated carboxylic acid involving a Ru(CH3COO)2[(R)-binap] catalyst
Yoshimura, Masahiro,Ishibashi, Yoshitaka,Miyata, Kengo,Bessho, Yuhki,Tsukamoto, Masaki,Kitamura, Masato
, p. 11399 - 11409 (2007)
Hydrogenation of (Z)-3-phenyl-2-butenoic acid with a Ru(CH3COO)2[(R)-binap] (BINAP=2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) catalyst in methanol gives (S)-3-phenyl-2-butanoic acid and its R enantiomer in a 97:3 (4 atm) to 94:6 (100 atm) ratio in quantitative yield. Both hydrogen gas and protic methanol participate in the saturation of the olefinic bond. Analysis of the products obtained using (Z)-3-phenyl-2-butenoic acid-3-13C and either H2, a 1:1 H2-D2 mixture, or D2 in CH3OD indicates that several catalytic cycles are operative, showing different reactivity and stereoselectivity. The major S enantiomer was formed primarily by the standard Ru monohydride mechanism, whereas the minor R isomer is produced via more complicated routes.
