Isoindolinones as Michael Donors under Phase Transfer Catalysis: Enantioselective Synthesis of Phthalimidines Containing a Tetrasubstituted Carbon Stereocenter

Molecules. 2015 May 12;20(5):8484-98. doi: 10.3390/molecules20058484.

Abstract

Readily available chiral ammonium salts derived from cinchona alkaloids have proven to be effective phase transfer catalysts in the asymmetric Michael reaction of 3-substituted isoindolinones. This protocol provides a convenient method for the construction of valuable asymmetric 3,3-disubstituted isoindolinones in high yields and moderate to good enantioselectivity. Diastereoselectivity was also investigated in the construction of contiguous tertiary and quaternary stereocenters. The use of acrolein as Michael acceptor led to an interesting tricyclic derivative, a pyrroloisoindolinone analogue, via a tandem conjugated addition/cyclization reaction.

Keywords: asymmetric catalysis; chiral phase transfer catalysts; conjugate addition; nitrogen heterocycles; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrolein / chemistry
  • Ammonium Compounds / chemistry
  • Carbon / chemistry
  • Catalysis
  • Cinchona Alkaloids / chemistry
  • Cyclization
  • Isoindoles / chemistry*
  • Molecular Structure
  • Phthalimides / chemical synthesis*
  • Phthalimides / chemistry*
  • Stereoisomerism

Substances

  • Ammonium Compounds
  • Cinchona Alkaloids
  • Isoindoles
  • Phthalimides
  • phthalimidine
  • Carbon
  • Acrolein