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.
Huang
Yi-Yong
YY
Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. China.
He
Yan-Mei
YM
Zhou
Hai-Feng
HF
Wu
Lei
L
Li
Bao-Lin
BL
Fan
Qing-Hua
QH
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