Chrome Extension
WeChat Mini Program
Use on ChatGLM

Regioselective Fluorohydrin Synthesis from Allylsilanes and Evidence for a Silicon–Fluorine Gauche Effect

Alexie W. Clover, Adam P. Jones,Robert F. Berger,Werner Kaminsky,Gregory. W. O'Neil

The Journal of Organic Chemistry(2024)

Western Washington Univ | Univ Washington

Cited 0|Views4
Abstract
Allylsilanes can be regioselectively transformed into the corresponding 3-silylfluorohydrin in good yield using a sequence of epoxidation followed by treatment with HF·Et3N with or without isolation of the intermediate epoxide. Various silicon-substitutions are tolerated, resulting in a range of 2-fluoro-3-silylpropan-1-ol products from this method. Whereas other fluorohydrin syntheses by epoxide opening using HF·Et3N generally require more forcing conditions (e.g., higher reaction temperature), opening of allylsilane-derived epoxides with this reagent occurs at room temperature. We attribute this rate acceleration along with the observed regioselectivity to a β-silyl effect that stabilizes a proposed cationic intermediate. The use of enantioenriched epoxides indicates that both SN1- and SN2-type mechanisms may be operable depending on substitution at silicon. Conformational analysis by NMR and theory along with a crystal structure obtained by X-ray diffraction points to a preference for silicon and fluorine to be proximal to one another in the products, perhaps favored due to electrostatic interactions.
More
Translated text
Key words
Enantioselective Fluorination,Enantioselective Synthesis
PDF
Bibtex
AI Read Science
Must-Reading Tree
Example
Generate MRT to find the research sequence of this paper
Related Papers
Gregory W. O'Neil, Inna A. Fomina,Christopher R. Myers, Cierra L. M. Soumis, Margaret L. Scheuermann, James McCarty,Timothy B. Clark
2022

被引用1 | 浏览

Data Disclaimer
The page data are from open Internet sources, cooperative publishers and automatic analysis results through AI technology. We do not make any commitments and guarantees for the validity, accuracy, correctness, reliability, completeness and timeliness of the page data. If you have any questions, please contact us by email: report@aminer.cn
Chat Paper
GPU is busy, summary generation fails
Rerequest