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Issue 12, 2012
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Preparation of aminomethyl functionalised silanes via an α-lithiated amine: From their synthesis, stability and crystal structures to stereochemical issues

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Abstract

The preparation of aminomethyl functionalised silanes based on the α-lithiated amine, (1R,2R)-N,N,N′,N′-tetramethylcyclohexane-1,2-diamine [(R,R)-TMCDA] is reported. This methodology can be applied for the synthesis of mono-aminomethyl substituted systems, but most remarkably also for di- and trifunctionalised compounds. The trapping of the lithiated amine is accompanied by transmetallation reactions resulting in the formation of (silylmethyl)silanes depending on the reaction temperature. The zinc(II) halide complexes of the mono-functionalised systems show the formation of exclusively one configuration of the stereogenic nitrogen atom, in which the spatially more demanding substituent exhibits the pseudo-equatorial position. The di- and trifunctionalised systems feature high sensitivity towards Si–C bond cleavage under re-formation of the (R,R)-TMCDA fragment.

Graphical abstract: Preparation of aminomethyl functionalised silanes via an α-lithiated amine: From their synthesis, stability and crystal structures to stereochemical issues

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Publication details

The article was received on 12 Nov 2011, accepted on 18 Dec 2011 and first published on 03 Feb 2012


Article type: Paper
DOI: 10.1039/C2DT12163H
Dalton Trans., 2012,41, 3452-3460

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    Preparation of aminomethyl functionalised silanes via an α-lithiated amine: From their synthesis, stability and crystal structures to stereochemical issues

    V. H. Gessner and C. Strohmann, Dalton Trans., 2012, 41, 3452
    DOI: 10.1039/C2DT12163H

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