Unusual Coordination Pattern of the Lithium Center in a Chiral alpha-Lithiated Silicon Compound

Bauer, Jonathan O. and Strohmann, Carsten (2021) Unusual Coordination Pattern of the Lithium Center in a Chiral alpha-Lithiated Silicon Compound. ORGANOMETALLICS, 40 (1). pp. 11-15. ISSN 0276-7333, 1520-6041

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Abstract

An understanding of how stereogenic centers can influence the construction of a new metalated chirality center requires profound investigations concerning coordination and aggregation effects. A racemic silicon-stereogenic aminomethoxysilane (2) was chosen as the starting compound, which is additionally equipped with a (trimethylsilyl)methylene bridge and an aminomethyl function. Metalation of 2 with tert-butyllithium led to the inversion-symmetric dimer (u-3)(2), which shows an unusual coordination mode with intramolecular agostic C-H center dot center dot center dot Li interactions capping the three-coordinate trigonal-planar lithium centers. Compound 3 was characterized by X-ray crystallography and NMR spectroscopy in solution. Reaction of the lithiated intermediate 3 with chlorotrimethylstannane provided the first insight into the configurational stability of the metalated stereogenic center.

Item Type: Article
Uncontrolled Keywords: PETERSON OLEFINATIONS; STEREOCHEMICAL COURSE; CRYSTAL-STRUCTURES; REAGENTS; BENZYLLITHIUM; REACTIVITY; COMPLEXES; MECHANISM; VAN
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Anorganische Chemie
Depositing User: Dr. Gernot Deinzer
Date Deposited: 01 Sep 2022 06:52
Last Modified: 01 Sep 2022 06:52
URI: https://pred.uni-regensburg.de/id/eprint/47146

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