Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: facile liquid/solid catalyst separation and application in asymmetric hydrogenation.
The thermomorphic BINAP derivative 1 tagged with long alkyl chains was prepared from (S)-5,5'-diamino BINAP and applied to Ru-catalyzed asymmetric hydrogenation of beta-ketoesters under homogeneous conditions in 3:1 (v/v) ethanol/1,4-dioxane at 60 degrees C with high enantioselectivity (up to 98% ee). Results indicated that the Ru(1) catalyst was easily recovered by simple cooling and precipitation and could be used for at least four cycles without any loss of enantioselectivity.
Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. China.
Yi-Yong
YY
Huang
Yan-Mei
YM
He
Hai-Feng
HF
Zhou
Lei
L
Wu
Bao-Lin
BL
Li
Qing-Hua
QH
Fan
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D006865:Hydrogenation; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism; D013696:Temperature
C419450:2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-Ru(OAc)2; D000438:Alcohols; D004952:Esters; D007659:Ketones; D008024:Ligands; D009942:Organometallic Compounds; D012428:Ruthenium