Chiral Silanediols in Anion-Binding Catalysis

Chiral Silanediols in Anion-Binding Catalysis

A perfect pair: Silanediols are effective catalysts for the addition of silyl ketene acetals to N‐acylisoquinolinium ions. Importantly, this is the first example of a silanediol plausibly participating in anion‐binding catalysis, a relatively new direction in the field of hydrogen‐bond‐donor catalys...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-10, Vol.52 (43), p.11321-11324
Hauptverfasser: Schafer, Andrew G., Wieting, Joshua M., Fisher, Thomas J., Mattson, Anita E.
Format: Artikel
Sprache:eng
Schlagworte:
Acetals
Catalysis
Catalysts
hydrogen bonds
ion pairs
Ketenes
organocatalysis
silicon
synthetic methods
Transformations
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Zusammenfassung:A perfect pair: Silanediols are effective catalysts for the addition of silyl ketene acetals to N‐acylisoquinolinium ions. Importantly, this is the first example of a silanediol plausibly participating in anion‐binding catalysis, a relatively new direction in the field of hydrogen‐bond‐donor catalysis. The chiral, enantiopure C2‐symmetric silanediol 1 catalyzes enantioselective transformations.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201305496