Catalytic enantioselective indium-mediated allylation of hydrazones

Org Lett. 2005 Jun 23;7(13):2767-70. doi: 10.1021/ol051160o.

Abstract

[reaction: see text] A facile and highly selective indium-mediated allylation of hydrazones utilizing BINOL ligands is described. Chiral (R)-3,3'-bistrifluoromethylBINOL afforded homoallylic amines in up to 97% ee with stoichiometric ligand. Employing only 10 mol % ligand afforded selectivity of up to 92% ee.

Publication types

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

MeSH terms

  • Catalysis
  • Hydrazones* / chemical synthesis
  • Hydrazones* / chemistry
  • Indium / chemistry*
  • Ligands
  • Molecular Structure
  • Naphthols / chemistry*
  • Stereoisomerism

Substances

  • BINOL, naphthol
  • Hydrazones
  • Ligands
  • Naphthols
  • Indium