Tandem halogenation/Michael-initiated ring-closing reaction of α,β-unsaturated nitriles and activated methylene compounds: one-pot diastereoselective synthesis of functionalized cyclopropanes

Org Biomol Chem. 2014 Apr 21;12(15):2427-35. doi: 10.1039/c4ob00087k.

Abstract

An efficient one-pot synthetic route to highly substituted cyclopropanes has been developed from readily available α,β-unsaturated nitriles and doubly activated methylene compounds under very mild conditions in a highly diastereoselective manner, which involves halogenation, Michael addition and intramolecular ring-closing reaction sequences.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry*
  • Halogenation*
  • Nitriles / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Cyclopropanes
  • Nitriles