Kuemper, Manuel and Goetz, Tobias and Espinosa-Jalapa, Noel Angel and Falk, Alexander and Rothfelder, Robin and Bauer, Jonathan O. (2023) Stereochemically Pure Si-Chiral Aminochlorosilanes. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 649 (16). e202300067. ISSN 0044-2313, 1521-3749
Full text not available from this repository. (Request a copy)Abstract
Silicon-based compounds with stereochemical information and convertible functional units are valuable building blocks in synthetic chemistry. Si-stereogenic aminochlorosilanes are built up by Si N bond formation between an achiral dichlorosilane and a chiral enantiomerically pure primary amine. Both diastereomers could be isolated as stereochemically pure single-crystals by fractional crystallization and were analyzed by X-ray crystallography. Defined intermolecular interaction patterns were identified illustrating the role of N H center dot center dot center dot pi, C H center dot center dot center dot pi, and N H center dot center dot center dot Cl contacts in the molecular crystalline packing arrangements. Stepwise functionalization of the silicon chlorine and silicon amine functions was carried out, demonstrating their potential for use as a chiral synthesis precursors. Via optically pure aminomethoxysilanes, enantiomerically enriched methoxysilanols, chloromethoxysilanes, and methoxysilanethiols were synthesized. The stereospecificity of the transformations was monitored. The (R)-BINOL-PSSLi method for determining the enantiomeric purity was found to be the tool of choice for acid-sensitive silanols and silanethiols.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | ASYMMETRIC SILICON; CRYSTAL-STRUCTURE; ALKOXYSILANES; CONVERSION; ACCESS; Aminochlorosilanes; Chirality; Interaction patterns; Silanols; Silicon |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Anorganische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 12 Mar 2024 10:11 |
| Last Modified: | 13 Mar 2024 08:56 |
| URI: | https://pred.uni-regensburg.de/id/eprint/59397 |
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