Non-racemic (scalemic) planar-chiral five-membered metallacycles: routes, means, and pitfalls in their synthesis and characterization

Chem Soc Rev. 2008 Feb;37(2):406-25. doi: 10.1039/b618557f. Epub 2007 Oct 8.

Abstract

This critical review provides a systematic classification of the synthetic routes to planar-chiral five-membered metallacycles into several routes, namely C-H bond activation, oxidative addition, transmetallation and optical resolution. As a characteristic of these bulk compounds is that they are synthesized as binary mixtures of enantiomers in proportions varying from the racemate to enantiopure, a review of absolute-configuration determination of the title planar-chiral scalemates is presented. This review is of interest to organic and organometallic synthetic chemists involved in asymmetric synthesis (97 references).

Publication types

  • Review

MeSH terms

  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Heterocyclic Compounds / classification
  • Molecular Conformation
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / classification
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Heterocyclic Compounds
  • Organometallic Compounds