Lewis Acids Catalyze the Addition of Allylboronates to Aldehydes by Electrophilic Activation of the Dioxaborolane in a Closed Transition Structure
- 23 March 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (14) , 4518-4519
- https://doi.org/10.1021/ja049446w
Abstract
This study addressed the mechanism of the recently reported Lewis acid-catalyzed manifold for additions of allylboronates to aldehydes. A series of control experiments using various reagents and conditions, and kinetic studies by low-temperature NMR spectroscopy, were performed to investigate the origin of the activation provided by the best catalyst, Sc(OTf)3. The results obtained are strongly supportive of a mechanism involving electrophilic boron activation by coordination of the metal ion to one of the boronate oxygens in a closed bimolecular transition state.Keywords
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