Straightforward stereoselective synthesis of spiro-epoxyoxindoles

Org Lett. 2007 Apr 26;9(9):1745-8. doi: 10.1021/ol070439x. Epub 2007 Mar 30.

Abstract

[reaction: see text] The in situ preparation of a sulfonium ylide reagent achieved the highly diastereoselective epoxidation of isatins, so that a new and straightforward access to biologically significant spiro-epoxyoxindoles is provided. The first investigations of an asymmetric version are reported with enantiopure sulfides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Epoxy Compounds
  • Indoles
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole
  • N-methylisatin