Preparation and diastereoselective ortho-metalation of chiral ferrocenyl imidazolines: remarkable influence of LDA as metalation additive

Org Lett. 2005 Sep 15;7(19):4137-40. doi: 10.1021/ol051437k.

Abstract

[reaction: see text] The preparation of optically pure ferrocenyl imidazolines starting from ferrocenecarboxylic acid and the application to diastereoselective ortho-metalations is described highlighting the remarkable influence of lithium dialkylamides, especially LDA, as metalation additives (in combination with tert-butyllithium) on the diastereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Crystallography, X-Ray
  • Imidazolines / chemical synthesis
  • Imidazolines / chemistry*
  • Iron / chemistry*
  • Ligands
  • Lithium Compounds / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism

Substances

  • Amides
  • Imidazolines
  • Ligands
  • Lithium Compounds
  • Iron