Substrate-Controlled, One-Pot Synthesis: Access to Chiral Chroman-2-one and Polycyclic Derivatives

Org Lett. 2016 Feb 19;18(4):864-7. doi: 10.1021/acs.orglett.6b00160. Epub 2016 Feb 4.

Abstract

Based on the appropriate choice of electrophiles, one-pot, multicomponent, enantioselective domino reactions have been realized which contain a five-step sequence and provide highly efficient access to potentially bioactive chroman-2-one derivatives as a single diastereoisomer with excellent enantioselectivities and in high yields. This new strategy could significantly improve the previous protocol by directly starting from commercial 2-hydroxybenzaldehydes rather than preformed lactols, which have to be synthesized in several additional steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chromones / chemical synthesis*
  • Chromones / chemistry
  • Molecular Structure
  • Polycyclic Aromatic Hydrocarbons / chemical synthesis*
  • Polycyclic Aromatic Hydrocarbons / chemistry
  • Stereoisomerism

Substances

  • Chromones
  • Polycyclic Aromatic Hydrocarbons