74850-77-4Relevant academic research and scientific papers
Syntheses of Novel Sugar Phosphine Derivatives, and Homogeneous Hydrogenation Reaction with Their Rhodium Complexes
Saito, Setsuo,Nakamura, Yushin,Morita, Yutaka
, p. 5284 - 5293 (2007/10/02)
Optically active diphenylphosphine derivatives, (1R,3R,4S,5R,6R)-6-cyano-5-diphenylphosphino-3,4-O-isopropylidene-2-oxabicycloheptane-3,4-diol (15) and its reduction product (17), were prepared by the cyclization of 12 or 13, which was obtained from a common sugar, D-glucose.These phosphines were used as ligands in the rhodium complex-catalyzed asymmetric hydrogenation of prochiral olefins.The rhodium complex catalyst which was constructed with 2 mol of 15 and 1 mol of rhodium(cyclooctene)2Cl (20) worked efficiently for the asymmetric hydrogenation of α-acetamidocinnamic acid (18) and itaconic acid (24) with 91.6percent ee-(S) and 69.6percent ee-(R), respectively.On the other hand, the rhodium complex constructed with 1 mol of 17 and 1 mol of 20 was less effective than that of 15, giving 39.0percent ee-(R) in the reaction with 18.Methyl esters of 18 and 24 were also hydrogenated using the complex of 15.Keywords - D-glucose; (1R,3R,4S,5R,6R)-6-cyano-5-diphenylphosphino-3,4-O-isopropylidene-2-oxabicycloheptane-3,4-diol; cyclobutane ring formation; chiral phosphine ligand; rhodium complex; asymmetric hydrogenation; enantioselectivity
ASSYMETRIC HYDROGENATION WITH CHIRAL PHOSPHINE LIGAND HAVING C-PPh2 BONDING DERIVED FROM D-GLUCOSE
Nakamura, Yushin,Saito, Setsuo,Morita, Yutaka
, p. 7 - 10 (2007/10/02)
Rh-complex of 6S-cyano-5R-diphenylphosphino-3R,4S-O-isopropylidene-2-oxa-bicycloheptane showed the relatively high enantioselectivity (S-configuration) in the hydrogenation of α-acetamidocinnamic acid, whereas Rh-complex of the 6S-aminomethyl compo
