Authors: | Langenohl, Felix Rösler, Jonas Zühlke, Sebastian Kirchhoff, Jan-Lukas Strohmann, Carsten |
Title: | A silicon-stereogenic silanol - 18O-isotope labeling and stereogenic probe reveals hidden stereospecific water exchange reaction |
Language (ISO): | en |
Abstract: | A silicon-stereogenic aminosilanol was isolated in excellent diastereomeric ratio and the absolute configuration was determined. The silanol is configurative and condensation stable in solution and shows stereoselective transformations with a clean stereospecific pathway in follow-up reactions, which leads to the isolation of a silicon-stereogenic zinc complex and siloxane compounds. Investigations with 18O-labelled water and mass spectrometry analysis revealed an otherwise hidden exchange of oxygen atoms of silanol and water in solution that proceeds with retention of the configuration at the silicon center. This novel combination of a stereochemical probe and isotopic labeling in a silicon-stereogenic compound opens new analytic possibilities to study stereochemical courses of reactions with the aid of chiral silanols mechanistically. |
Subject Headings: | Chirality Configuration Isotopic labelling Silanols Silicon |
URI: | http://hdl.handle.net/2003/42266 http://dx.doi.org/10.17877/DE290R-24103 |
Issue Date: | 2022-09-27 |
Rights link: | https://creativecommons.org/licenses/by/4.0/ |
Appears in Collections: | Lehrstühle für Anorganische Chemie |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
Chemistry A European J - 2022 - Langenohl - A Silicon‐Stereogenic Silanol ‐ 18O‐Isotope Labeling and Stereogenic Probe.pdf | DNB | 2.05 MB | Adobe PDF | View/Open |
This item is protected by original copyright |
This item is licensed under a Creative Commons License