Recent advances and new concepts for the synthesis of axially stereoenriched biaryls

Chem Soc Rev. 2015 Jun 7;44(11):3418-30. doi: 10.1039/c5cs00012b.

Abstract

Axial chirality is a key feature of many important organic molecules, such as biologically active compounds, stereogenic ligands and optically pure materials. Significant efforts in the field of the atropisomeric synthesis of biaryls have hence been undertaken over the past decade. Several major improvements of the already known methods to build up such chiral backbones (e.g. oxidative couplings and stereoselective Suzuki-Miyaura arylations) have been achieved and, in parallel, novel concepts have emerged enabling unprecedented synthetic routes toward molecules of this kind. These outstanding steps further unlocked the door to the preparation of previously difficult-to-access precursors of privileged ligands like BINOL, BINAM, QUINAP and many other molecules of interest.

Publication types

  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • 4-Butyrolactone / analogs & derivatives
  • Gossypol
  • Lignans
  • Models, Molecular*
  • Organic Chemicals / chemical synthesis*
  • Organic Chemicals / chemistry*
  • Stereoisomerism
  • Vancomycin

Substances

  • Lignans
  • Organic Chemicals
  • steganacin
  • Vancomycin
  • Gossypol
  • 4-Butyrolactone