N-Heterocyclic carbene-catalyzed [4 + 2] cyclization of 2-bromo-2-enal with 3-alkylenyloxindoles: efficient assembly of spirocarbocyclic oxindole

Org Biomol Chem. 2015 Feb 14;13(6):1829-35. doi: 10.1039/c4ob01706d.

Abstract

A NHC-catalyzed [4 + 2] cyclization of 2-bromo-2-enal bearing γ-H with 3-alkylenyloxindoles under mild reaction conditions gives spirocarbocyclic oxindoles containing one quaternary carbon in moderate to good yields with high diastereoselectivities. The easy availability of the starting materials, the concise assembly and the potential utilization value of the products make this strategy attractive in molecular biology and pharmacy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Molecular Structure
  • Oxindoles
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

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