N719 dye-sensitized organophotocatalysis: enantioselective tandem Michael addition/oxyamination of aldehydes

Org Lett. 2012 Jul 6;14(13):3272-5. doi: 10.1021/ol3011858. Epub 2012 Jun 8.

Abstract

A remarkably efficient photosensitizer, N719 dye, was used in asymmetric tandem Michael addition/oxyamination of aldehydes, rendering α,β-substituted aldehydes in good yields with excellent levels of enantioselectivity and diastereoselectivity. This is the first report of a multiorganocatalytic reaction involving iminium catalysis and photoinduced singly occupied molecular orbital (SOMO) catalysis. This reaction is expected to expand the scope of tandem organocatalytic reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry*
  • Amination
  • Catalysis
  • Coloring Agents / chemistry*
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Photochemical Processes
  • Photosensitizing Agents / chemistry*
  • Stereoisomerism
  • Thiocyanates / chemistry*

Substances

  • Aldehydes
  • Coloring Agents
  • Organometallic Compounds
  • Photosensitizing Agents
  • Thiocyanates
  • bis(2,2'-bipyridyl-4,4'-dicarboxylate)ruthenium(II) bis(tetrabutylammonium) bis(thiocyanate)