Asymmetric [3 + 2] annulation of N-protected isatins with but-3-yn-2-one catalyzed by DIOP: facile creation of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione

Org Biomol Chem. 2012 Oct 28;10(40):8048-50. doi: 10.1039/c2ob25801c.

Abstract

DIOP catalyzed highly enantioselective [3 + 2] annulation of N-protected isatins with but-3-yn-2-one has been disclosed, allowing the synthesis of enantioenriched spiro[furan-2,3'-indoline]-2',4(5H)-dione in moderate yields along with good to high enantioselectivities under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Dioxolanes / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Isatin / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Phosphines / chemistry*
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Dioxolanes
  • Indoles
  • Ketones
  • Phosphines
  • Spiro Compounds
  • Isatin