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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

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Published on: October 18, 2019

Chiral silanediols in anion-binding catalysis.

Andrew G Schafer¹, Joshua M Wieting, Thomas J Fisher

¹Department of Chemistry and Biochemistry, The Ohio State University, 100 W. 18th Ave., Columbus, OH 43210 (USA) http://mattson.group.chemistry.ohio-state.edu/

Angewandte Chemie (International Ed. in English)

|September 17, 2013

Summary

This summary is machine-generated.

Silanediols efficiently catalyze reactions between silyl ketene acetals and N-acylisoquinolinium ions. This study introduces silanediols as catalysts in anion-binding catalysis, a novel approach in hydrogen-bond-donor catalysis for enantioselective transformations.

Keywords:

hydrogen bonds ion pairs organocatalysis silicon synthetic methods

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Published on: November 27, 2015

Area of Science:

Organic Chemistry
Catalysis
Asymmetric Synthesis

Background:

Hydrogen-bond-donor catalysis is a growing field.
Anion-binding catalysis is a relatively new area within catalysis.
Silanediols have not been previously explored for anion-binding catalysis.

Purpose of the Study:

To investigate the catalytic activity of silanediols.
To explore the use of silanediols in anion-binding catalysis.
To achieve enantioselective synthesis using silanediol catalysts.

Main Methods:

Utilizing silanediols as catalysts.
Employing silyl ketene acetals as nucleophiles.
Reacting with N-acylisoquinolinium ions as electrophiles.
Employing chiral, enantiopure C2-symmetric silanediol 1.

Main Results:

Silanediols were found to be effective catalysts.
The reaction involves the addition of silyl ketene acetals to N-acylisoquinolinium ions.
This represents the first plausible example of silanediol-mediated anion-binding catalysis.
Chiral silanediol 1 successfully catalyzed enantioselective transformations.

Conclusions:

Silanediols are effective catalysts for the addition reaction.
Silanediols can plausibly participate in anion-binding catalysis.
This work opens new avenues for hydrogen-bond-donor catalysis using silanediols.