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Issue 12, 2012
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Preparation of aminomethyl functionalised silanesvia 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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Supplementary files

Article information


Submitted
12 Nov 2011
Accepted
18 Dec 2011
First published
03 Feb 2012

Dalton Trans., 2012,41, 3452-3460
Article type
Paper

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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