Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to nitroalkenes

J Org Chem. 2006 Sep 15;71(19):7494-7. doi: 10.1021/jo0613838.

Abstract

A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form the cyclopropane in the presence of DBU under carefully controlled reaction conditions with outstanding diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Cyclization
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkenes
  • Cyclopropanes
  • Nitro Compounds