Thermomorphic system with non-fluorous phase-tagged Ru(BINAP) catalyst: facile liquid/solid catalyst separation and application in asymmetric hydrogenation

J Org Chem. 2006 Mar 31;71(7):2874-7. doi: 10.1021/jo052092m.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Catalysis
  • Esters / chemistry*
  • Hydrogenation
  • Ketones / chemistry*
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Ruthenium / chemistry
  • Stereoisomerism
  • Temperature*

Substances

  • 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl-Ru(OAc)2
  • Alcohols
  • Esters
  • Ketones
  • Ligands
  • Organometallic Compounds
  • Ruthenium