Asymmetric synthesis of a structurally and stereochemically complex spirooxindole pyran scaffold through an organocatalytic multicomponent cascade reaction

Chem Commun (Camb). 2012 Nov 4;48(85):10487-9. doi: 10.1039/c2cc36011j.

Abstract

A novel and convenient organocatalytic tandem reaction has been developed for the asymmetric assembly of saturated aldehydes (or enals), nitroolefins and isatins to produce six-membered oxa-spirooxindole backbones bearing four contiguous stereogenic centers and multiple functional groups with high stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Catalysis
  • Cycloaddition Reaction
  • Indoles / chemistry*
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Spiro Compounds / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Alkenes
  • Indoles
  • Pyrans
  • Spiro Compounds
  • indole