Application of a chiral scaffolding ligand in catalytic enantioselective hydroformylation

J Am Chem Soc. 2010 Oct 27;132(42):14757-9. doi: 10.1021/ja107433h.

Abstract

The synthesis of β-amino-aldehydes has been achieved through enantioselective hydroformylation of PMP-protected allylic amines. The reaction is accomplished by using a scalemic scaffolding ligand that covalently and reversibly binds to the substrate. These ligands behave like chiral auxiliaries because they are covalently attached to the substrate during hydroformylation; however, similar to traditional asymmetric ligands, they can be used in catalytic quantities. The directed hydroformylation of disubstituted olefins occurs under mild conditions (35 °C and 50 psi CO/H(2)), and Z-olefins afford excellent enantioselectivities (up to 93% 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.

MeSH terms

  • Catalysis
  • Formates / chemistry*
  • Ligands
  • Models, Molecular
  • Stereoisomerism

Substances

  • Formates
  • Ligands
  • formic acid