Expedient access to substituted 3-amino-2-cyclopentenones by dirhodium-catalyzed [3+2]-annulation of silylated ketene imines and enoldiazoacetates

Chem Commun (Camb). 2014 Mar 7;50(19):2462-4. doi: 10.1039/c3cc48993k. Epub 2014 Jan 23.

Abstract

In a reaction that proceeds under mild conditions with remarkable functional group tolerance, structurally diverse 3-amino-2-cyclopentenones bearing a quaternary carbon at the 4-position have been synthesized through a formal [3+2]-cycloaddition reaction of silylated ketene imines (SKIs) and enoldiazoaceates by dirhodium catalysis.

Publication types

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

MeSH terms

  • Acetates / chemistry*
  • Catalysis
  • Cycloaddition Reaction
  • Cyclopentanes / chemistry*
  • Diazonium Compounds / chemistry*
  • Ethylenes / chemistry
  • Imines / chemistry*
  • Ketones / chemistry
  • Rhodium / chemistry*

Substances

  • Acetates
  • Cyclopentanes
  • Diazonium Compounds
  • Ethylenes
  • Imines
  • Ketones
  • Rhodium
  • ketene