Photocatalytic [2 + 2] cycloadditions of enones with cleavable redox auxiliaries

Org Lett. 2012 Feb 17;14(4):1110-3. doi: 10.1021/ol3000298. Epub 2012 Feb 9.

Abstract

α,β-Unsaturated 2-imidazolyl ketones undergo [2 + 2] cycloaddition with a variety of Michael acceptors upon irradiation with visible light in the presence of Ru(bpy)(3)(2+). Cleavage of the imidazolyl auxiliary from the cycloadducts affords cyclobutane carboxamides, esters, thioesters, and acids that would not be accessible from direct cycloaddition of the corresponding unsaturated carbonyl compounds.

Publication types

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

MeSH terms

  • Catalysis
  • Cyclization
  • Dimerization
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemical Processes*