N-Heterocyclic carbene-catalyzed chemoselective cross-aza-benzoin reaction of enals with isatin-derived ketimines: access to chiral quaternary aminooxindoles

Org Lett. 2014 Jun 20;16(12):3272-5. doi: 10.1021/ol501286e. Epub 2014 May 30.

Abstract

A chemo- and enantioselective cross-aza-benzoin reaction between enals and isatin-derived ketimines is disclosed. The high chemoselectivity (of the acyl anion reaction over enal α- and β-carbon reactions) is enabled by the electronic and steric properties of the N-heterocyclic carbene organocatalyst.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Benzoin / chemistry*
  • Catalysis
  • Imines / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Isatin / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Nitriles / chemistry*
  • Stereoisomerism

Substances

  • Aza Compounds
  • Imines
  • Indoles
  • Nitriles
  • ketimine
  • carbene
  • Isatin
  • Benzoin
  • Methane