Direct enantioselective vinylogous aldol-cyclization cascade reaction of allyl pyrazoleamides with isatins: asymmetric construction of spirocyclic oxindole-dihydropyranones

Chem Commun (Camb). 2014 Sep 25;50(74):10790-2. doi: 10.1039/c4cc04235b.

Abstract

The first enantioselective vinylogous aldol-cyclization cascade reaction of allyl pyrazoleamides with isatins is reported. With 1 mol% of Takemoto catalyst, optically active spirocyclic oxindole-dihydropyranones were obtained in excellent yields (93-99%) and good-to-excellent enantioselectivities (82-97% ee).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amides / chemistry*
  • Catalysis
  • Cyclization
  • Indoles / chemistry*
  • Isatin / chemistry*
  • Oxindoles
  • Pyrans / chemistry*
  • Pyrazoles / chemistry
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Amides
  • Indoles
  • Oxindoles
  • Pyrans
  • Pyrazoles
  • Spiro Compounds
  • 2-oxindole
  • Isatin
  • 3-hydroxybutanal