Diastereoselective Synthesis of Spirocyclopropanes under Mild Conditions via Formal [2 + 1] Cycloadditions Using 2,3-Dioxo-4-benzylidene-pyrrolidines

Molecules. 2017 Feb 22;22(2):328. doi: 10.3390/molecules22020328.

Abstract

A highly diastereoselective cyclopropanation of cyclic enones with sulfur ylides was developed under catalyst-free conditions, producing multifunctional spirocyclopropanes in generally excellent yields (up to 99% yield and >99:1 d.r.). The asymmetric version of this method was realized by using an easily available chiral sulfur ylide, affording products with moderate to good stereoselectivity.

Keywords: catalyst free; diastereoselective synthesis; spirocyclopropanes; sulfur ylide.

MeSH terms

  • Benzylidene Compounds / chemistry*
  • Catalysis
  • Cycloaddition Reaction*
  • Cyclopropanes / chemical synthesis*
  • Cyclopropanes / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrrolidines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Sulfur / chemistry

Substances

  • Benzylidene Compounds
  • Cyclopropanes
  • Pyrrolidines
  • Spiro Compounds
  • Sulfur