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A Silicon-Stereogenic Silanol - 18 O-Isotope Labeling and Stereogenic Probe Reveals Hidden Stereospecific Water Exchange Reaction.

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 18 O-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.

SUBMITTER: Langenohl F 

PROVIDER: S-EPMC10100314 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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A Silicon-Stereogenic Silanol - <sup>18</sup> O-Isotope Labeling and Stereogenic Probe Reveals Hidden Stereospecific Water Exchange Reaction.

Langenohl Felix F   Rösler Jonas J   Zühlke Sebastian S   Kirchhoff Jan-Lukas JL   Strohmann Carsten C  

Chemistry (Weinheim an der Bergstrasse, Germany) 20221110 1

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 <sup>18</sup> O-labelled water and mass spectrometry analysis revealed an otherwise hidden ex  ...[more]

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