Asymmetric enamide hydrogenation using phosphinite thioglycosides: synthesis of D- and L-aminoesters using D-sugars as catalyst precursors

Org Lett. 2008 Sep 4;10(17):3697-700. doi: 10.1021/ol801301x. Epub 2008 Jul 29.

Abstract

Diastereomerically pure cationic Rh(I) complexes derived from phosphinite thioglycosides I were used as catalysts in highly enantioselective hydrogenations of enamides. The conformational similarity of alpha-D-arabinopyranose with beta-L-galactopyranose allows the synthesis of both enantiomers of alpha-amino acid derivatives such as D- and L-DOPA in excellent ee (97% and 98%), using derivatives of the former sugar as catalyst precursors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amides / chemistry*
  • Amines / chemical synthesis
  • Arabinose / chemistry
  • Carbohydrate Conformation
  • Carbohydrates / chemistry*
  • Catalysis
  • Dihydroxyphenylalanine / chemical synthesis
  • Dihydroxyphenylalanine / chemistry
  • Esters / chemical synthesis
  • Galactose / chemistry
  • Hydrogenation
  • Phosphinic Acids / chemistry*
  • Rhodium / chemistry
  • Stereoisomerism
  • Thioglycosides / chemistry*

Substances

  • Alkenes
  • Amides
  • Amines
  • Carbohydrates
  • Esters
  • Phosphinic Acids
  • Thioglycosides
  • Dihydroxyphenylalanine
  • Arabinose
  • Rhodium
  • Galactose