Volume 90 Issue 12 | p. 36 | Concentrates
Issue Date: March 19, 2012

Cage-Shaped Borate Catalyst Recognizes Aromatic Aldehydes

Lewis acid catalyst with an enzymelike binding pocket selects aromatic aldehydes over aliphatic aldehydes in Diels-Alder reactions
Department: Science & Technology
Keywords: organocatalyst, molecular recognition, Lewis acid, Diels-Alder reaction, enzyme

A boron-based organocatalyst with an enzymelike π-binding pocket has been designed to catch and hold aromatic aldehydes to facilitate Diels-Alder cycloaddition reactions. The research team led by Makoto Yasuda and Akio Baba of Japan’s Osaka University believes this is the first reported example of the molecular recognition of an aromatic aldehyde over an aliphatic aldehyde in a catalytic manner. Yasuda, Baba, and coworkers previously designed cage-shaped triphenylborate Lewis acids, such as B(OC6H4)3CH, . . .

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