Efficient asymmetric hydrogenation of olefins with hydrazine-derived diphosphoramidites

Org Biomol Chem. 2007 Oct 21;5(20):3340-6. doi: 10.1039/b710576b. Epub 2007 Sep 14.

Abstract

Enantiopure, BINOL-derived diphosphoramidites built upon an achiral hydrazine spacer are efficient ligands for the hydrogenation of 2-(acetylamino)-3-(aryl)-propenoic methyl esters. The activity and enantioselectivity of the hydrazine derivatives were shown to be markedly influenced by the nature of the two NR substituents, symmetrical but bulky R groups leading to the best results. A diphosphosphoramidite obtained from (t)BuHNNH(t)Bu resulted in ee's as high as 95%. The present results contradict previous reports on "short" diphosphoramidites.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Hydrazines / chemistry*
  • Hydrogenation
  • Ligands
  • Naphthols / chemistry*
  • Organophosphorus Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • BINOL, naphthol
  • Hydrazines
  • Ligands
  • Naphthols
  • Organophosphorus Compounds
  • phosphoramidite