A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction

J Am Chem Soc. 2003 Oct 22;125(42):12692-3. doi: 10.1021/ja0373871.

Abstract

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

Publication types

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

MeSH terms

  • Acetates / chemistry
  • Alcohols / chemical synthesis*
  • Catalysis
  • Copper / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Nitro Compounds / chemical synthesis*
  • Nitroparaffins / chemistry
  • Organometallic Compounds / chemistry
  • Oxazoles / chemistry*
  • Stereoisomerism

Substances

  • Acetates
  • Alcohols
  • Nitro Compounds
  • Nitroparaffins
  • Organometallic Compounds
  • Oxazoles
  • Copper
  • Methane
  • nitromethane