Organocatalytic Atroposelective Friedländer Quinoline Heteroannulation

Org Lett. 2019 Jun 21;21(12):4831-4836. doi: 10.1021/acs.orglett.9b01731. Epub 2019 Jun 10.

Abstract

An atroposelective Friedländer heteroannulation reaction of 2-aminoaryl ketones with α-methylene carbonyl derivatives has been developed for the first time with chiral phosphoric acid as an efficient organocatalyst. The desired enantioenriched axially chiral polysubstituted 4-arylquinoline architectures were prepared with good to high yields and enantioselectivities (up to 94% yield and up to 97% ee). Furthermore, the products can be readily derivatized to afford an array of new quinoline-containing heteroatropisomers, which hold great potential in asymmetric catalysis and drug discovery.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Ketones / chemistry*
  • Molecular Structure
  • Phosphoric Acids / chemistry*
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

  • Ketones
  • Phosphoric Acids
  • Quinolines
  • phosphoric acid
  • quinoline