Overcoming the Naphthyl Requirement in Stereospecific Cross-Couplings to Form Quaternary Stereocenters

J Am Chem Soc. 2021 Jun 16;143(23):8608-8613. doi: 10.1021/jacs.1c03898. Epub 2021 Jun 1.

Abstract

The use of a simple stilbene ligand has enabled a stereospecific Suzuki-Miyaura cross-coupling of tertiary benzylic carboxylates, including those lacking naphthyl substituents. This method installs challenging all-carbon diaryl quaternary stereocenters in good yield and ee and represents an important breakthrough in the "naphthyl requirement" that pervades stereospecific cross-couplings involving enantioenriched electrophiles.

Publication types

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

MeSH terms

  • Carboxylic Acids / chemistry*
  • Ligands
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism
  • Stilbenes / chemistry*

Substances

  • Carboxylic Acids
  • Ligands
  • Naphthalenes
  • Stilbenes