Rapid access to spirocylic oxindoles: application of asymmetric N-heterocyclic carbene-catalyzed [3 + 3] cycloaddition of imines to oxindole-derived enals

Org Lett. 2015 May 15;17(10):2318-21. doi: 10.1021/acs.orglett.5b00726. Epub 2015 May 4.

Abstract

A chiral N-heterocyclic carbene (NHC)-catalyzed [3 + 3] cycloaddition reaction of imines and oxindole-derived enals was developed for rapid access to spirocylic oxindoles. In most cases, the desired spirocylic oxindole products were obtained in high yields and excellent enantioselectivities with less than 1 h of reaction time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Cycloaddition Reaction
  • Heterocyclic Compounds / chemistry*
  • Imines / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Heterocyclic Compounds
  • Imines
  • Indoles
  • Oxindoles
  • Spiro Compounds
  • 2-oxindole
  • carbene
  • Methane