Atroposelective Desymmetrization of Resorcinol-Bearing Quinazolinones via Cu-Catalyzed C-O Bond Formation

Org Lett. 2022 Jan 21;24(2):762-766. doi: 10.1021/acs.orglett.1c04266. Epub 2022 Jan 10.

Abstract

Enantioselective Cu-catalyzed C-O cross coupling reactions yielding atropisomeric resorcinol-bearing quinazolinones have been developed. Utilizing a new guanidinylated dimeric peptidic ligand, a set of products were generated in good yields with excellent stereocontrol. The transformation was readily scalable, and a range of product derivatizations were performed.

MeSH terms

  • Catalysis
  • Copper* / chemistry
  • Molecular Structure
  • Quinazolinones* / chemical synthesis
  • Quinazolinones* / chemistry
  • Resorcinols* / chemistry
  • Stereoisomerism

Substances

  • Copper
  • Quinazolinones
  • Resorcinols
  • resorcinol