Jump to main content
Jump to site search

Issue 1, 2014
Previous Article Next Article

Computational study of diastereoselective ortho-lithiations of chiral ferrocenes

Author affiliations

Abstract

Diastereoselective ortho-lithiations serve for the preparation of many important chiral ferrocenes, however diastereoselections of these lithiations are explained only by simple steric models. We elucidated ortho-lithiations of three important ferrocenes based on DFT calculations. The calculations showed that simple models of transition states involving ferrocenyl substrates and lithium bases can only in some cases account for the experimental results. Transition state models, which include solvent or coordinating additives as distinct entities bound to lithium, can satisfactorily explain diastereoselection of the ortho-lithiations of chiral ferrocenes.

Graphical abstract: Computational study of diastereoselective ortho-lithiations of chiral ferrocenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 29 Jun 2013, accepted on 03 Oct 2013 and first published on 04 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41339J
Citation: Org. Biomol. Chem., 2014,12, 132-140
  •   Request permissions

    Computational study of diastereoselective ortho-lithiations of chiral ferrocenes

    A. Škvorcová and R. Šebesta, Org. Biomol. Chem., 2014, 12, 132
    DOI: 10.1039/C3OB41339J

Search articles by author

Spotlight

Advertisements