Stereoselective synthesis of highly functionalized nitrocyclopropanes through the organocatalyic Michael-addition-initiated cyclization of bromonitromethane and β,γ-unsaturated α-ketoesters

Chem Asian J. 2013 Nov;8(11):2859-63. doi: 10.1002/asia.201300778. Epub 2013 Aug 9.

Abstract

A highly diastereo- and enantioselective cyclopropanation of β,γ-unsaturated α-ketoesters with bromonitromethane has been successfully developed through a domino Michael-addition/intramolecular-alkylation strategy. Acceptable yields (up to 89%) and enantioselectivities (up to 96% ee) have been obtained.

Keywords: Michael addition; alkylation; asymmetric catalysis; nitrocyclopropanes; organocatalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Crystallography, X-Ray
  • Cyclization
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry*
  • Esters
  • Ethane / analogs & derivatives*
  • Ethane / chemistry
  • Molecular Conformation
  • Nitro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Cyclopropanes
  • Esters
  • Nitro Compounds
  • bromonitromethane
  • Ethane