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Issue 1, 2014
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Computational study of diastereoselective ortho-lithiations of chiral ferrocenes

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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

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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
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    Computational study of diastereoselective ortho-lithiations of chiral ferrocenes

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

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