Molecules (Feb 2017)

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

  • Yi Li,
  • Qing-Zhu Li,
  • Li Huang,
  • Hong Liang,
  • Kai-Chuan Yang,
  • Hai-Jun Leng,
  • Yue Liu,
  • Xu-Dong Shen,
  • Xiao-Jun Gou,
  • Jun-Long Li

DOI
https://doi.org/10.3390/molecules22020328
Journal volume & issue
Vol. 22, no. 2
p. 328

Abstract

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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