Issue 88, 2014

Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis

Abstract

Highly enantioselective protonation of α-halo and alkoxy carboxylic acid-derived ketene disilyl acetals is achieved by using P-spiro chiral diaminodioxaphosphonium barfate as a Brønsted acid catalyst, where the enantiofacial discrimination by the catalyst mainly stems from the recognition of the electronic difference between two substituents on the ketene disilyl acetal.

Graphical abstract: Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis

Supplementary files

Article information

Article type
Communication
Submitted
04 Aug 2014
Accepted
08 Sep 2014
First published
10 Sep 2014

Chem. Commun., 2014,50, 13489-13491

Author version available

Enantioselective protonation of α-hetero carboxylic acid-derived ketene disilyl acetals under chiral ionic Brønsted acid catalysis

D. Uraguchi, T. Kizu, Y. Ohira and T. Ooi, Chem. Commun., 2014, 50, 13489 DOI: 10.1039/C4CC06081D

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