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

Chem Commun (Camb)

Institute of Transformative Bio-Molecules (WPI-ITbM) and Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho B2-3(611), Chikusa, Nagoya 464-8603, Japan.

Published: November 2014

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.

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Source
http://dx.doi.org/10.1039/c4cc06081dDOI Listing

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