A convenient synthesis and the asymmetric hydrogenation of N-phthaloyl dehydroamino acid esters

Org Lett. 2008 Jul 17;10(14):3033-6. doi: 10.1021/ol800996j. Epub 2008 Jun 13.

Abstract

A convenient synthetic method was reported for the preparation of N-phthaloyl dehydroamino acid esters from easily accessible vinyl bromides (or vinyl tosylate) and potassium phthalimide. Rh-catalyzed asymmetric hydrogenation of these substrates with TangPhos gave the products with good to excellent enantioselectivities (up to 99% ee).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Esters
  • Hydrogenation
  • Molecular Structure
  • Phthalic Acids / chemistry*
  • Rhodium / chemistry*
  • Stereoisomerism
  • Vinyl Compounds / chemistry

Substances

  • Amino Acids
  • Esters
  • Phthalic Acids
  • Vinyl Compounds
  • Rhodium