Unexpected catalytic reactions of silyl-protected enol diazoacetates with nitrile oxides that form 5-arylaminofuran-2(3H)-one-4-carboxylates

Org Lett. 2012 Feb 3;14(3):800-3. doi: 10.1021/ol203331r. Epub 2012 Jan 24.

Abstract

Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetals / chemistry*
  • Amination
  • Azo Compounds / chemistry*
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Furans / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Oxides / chemistry*

Substances

  • Acetals
  • Azo Compounds
  • Carboxylic Acids
  • Furans
  • Nitriles
  • Oxides
  • furan