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Angew Chem Int Ed Engl. 2014 Jul 28;53(31):8167-71. doi: 10.1002/anie.201404255. Epub 2014 Jun 18.

From an α-functionalized silicon-stereogenic N,O-silane to a monomeric and tetracoordinate tBuLi adduct with lithium-centered chirality.

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  • 1Anorganische Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund (Germany).


Donor-functionalized silanes with stereogenic silicon centers are extremely rare. A convenient stereocontrolled route to a nitrogen-oxygen-functionalized silicon-chiral compound with an additional aminomethyl function is presented. This silane was directly achieved in stereochemically pure form by a simple nucleophilic substitution reaction. Owing to the unique asymmetry of this silane and the presence of three donor functions, the first monomeric butyllithium compound with lithium-centered chirality could be isolated; the configuration was assigned by X-ray crystallography. This [silane⋅ tBuLi] complex undergoes an unexpected deprotonation/stereospecific substitution sequence in toluene, leading to the development of a convenient one-pot synthesis of a functionalized silicon-chiral benzylsilane, which proceeds with inversion of configuration and complete preservation of the stereochemical integrity at silicon.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


alkyllithium compounds; chirality; reactive intermediates; silanes; silicon

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