Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group

Org Lett. 2017 Sep 1;19(17):4424-4427. doi: 10.1021/acs.orglett.7b01776. Epub 2017 Aug 15.

Abstract

An efficient and stereospecific Pd-catalyzed protocol for the C-H arylation of pyroglutamic acid derivatives that uses 8-aminoquinoline as a directing group is described. The reaction was shown to proceed efficiently with a variety of aryl and heteroaryl iodides bearing different functional groups, giving C3-arylated cis products in good to high yields. Removal of the 8-aminoquinoline unit from these C-H arylation products enables access to synthetically useful cis and trans pyroglutamic acid-based building blocks.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aminoquinolines
  • Catalysis
  • Molecular Structure
  • Palladium / chemistry*
  • Pyrrolidonecarboxylic Acid
  • Stereoisomerism

Substances

  • Aminoquinolines
  • Palladium
  • Pyrrolidonecarboxylic Acid
  • 8-aminoquinoline