115261-98-8Relevant academic research and scientific papers
SYNTHESIS AND APPLICATION OF A NOVEL BISPHOSPHINE LIGAND, (-)-DIOCP, AS AN UNSYMMETRIZED DIOP TO PROVE THE GENERAL UTILITY OF NEW DESIGNING CONCEPT.
Chiba, Mitsuo,Takahashi, Hitoe,Takahashi, Hisashi
, p. 3675 - 3678 (1987)
A new chiral bisphosphine-Rh complex (DIOCP-Rh) was found to show excellent catalytic activity and good enantioselectivity for the asymmetric hydrogenation of ketopantolactone proving the general utility of new designing concept.
Synthesis of efficient chiral bisphosphine ligands, modified DIOPs, (4R,5R)-4-(Diaryl- or dialkylphosphino)methyl-5-(diarylphosphino)methyl-2,2- dimethyl-1,3-dioxolanes, and their use in rhodium(I)-catalyzed asymmetric hydrogenations
Morimoto,Chiba,Achiwa
, p. 1149 - 1156 (2007/10/02)
Modified DIOPs, (4R,5R)-4-(diaryl- or dialkyphosphino)methyl-5- (diarylphosphino)methyl-2,2-dimethyl-1,3-dioxolanes, were prepared on the basis of our design concept, and used as ligands for the rhodium(I)-catalyzed asymmetric hydrogenations of ketopantolactone, itaconic acid, dimethyl itaconate, and β-aryl-substituted itaconic acid derivatives. A neutral rhodium(I)-complex of (4R-trans)-dicyclohexyl[[5- [(diphenylphosphino)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]phosphine (DIOCP) bearing both a dicyclohexylphosphino group and a diphenylphosphino group was found to be a more efficient catalyst than the original DIOP in the asymmetric hydrogenation of ketopantolactone. Modified DIOPs bearing electron-donating groups at their para positions were efficient ligands for the rhodium(I)-catalyzed assymetric hydrogenations of itaconic acid and its derivatives; in particular, (4R-trans)-[(2,2-dimethyl-1,3-dioxolane-4,5- diyl)bis(methylene)]bis[bis(4'-methoxy-3',5'-dimethylphenyl)phosphine] (MOD- DIOP) bearing both a p-methoxy group and two m,m'-methyl groups on each phenyl group showed much higher enantioselectivity and catalytic activity than DIOP.
